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Wender Taxol total synthesis

Index Wender Taxol total synthesis

The Wender Taxol total synthesis in organic chemistry describes a Taxol total synthesis (one of six to date) by the group of Paul Wender at Stanford University published in 1997. [1]

100 relations: Acetate, Acetic acid, Acetic anhydride, Acetonide, Acyloin, Alcohol, Aldehyde, Aldol reaction, Alkene, Alkylation, Alkyne, Allyl bromide, Alpha-Pinene, Ammonium chloride, Ammonium fluoride, Benzoic acid, Bromine, Carbonate ester, Catalytic cycle, Chemical trap, Chloroalkyl ether, Chrysanthenone, Convergent synthesis, Crabtree's catalyst, DABCO, Danishefsky Taxol total synthesis, Deprotonation, Dess–Martin periodinane, Diene, Diol, English Canada, Epoxide, Eschenmoser's salt, Ester, Gilman reagent, Grignard reaction, Grob fragmentation, Holton Taxol total synthesis, Homologous series, Hydrochloric acid, Hydrogen, Imidazole, In situ, Isomerization, Journal of the American Chemical Society, Ketone, Kuwajima Taxol total synthesis, Lithium aluminium hydride, Lithium bromide, Lithium diisopropylamide, ..., Mesylate, Meta-Chloroperoxybenzoic acid, Methanesulfonyl chloride, Methanol, Methoxymethylenetriphenylphosphine, Methylene group, Mukaiyama Taxol total synthesis, N,N-Diisopropylethylamine, N-Methylmorpholine N-oxide, Nicolaou Taxol total synthesis, Nucleophilic addition, Nucleophilic conjugate addition, Nucleophilic substitution, Ojima lactam, Organic chemistry, Organic redox reaction, Osmium tetroxide, Oxaziridine, Oxetane, Ozonolysis, Paclitaxel total synthesis, Paul Wender, Phenyllithium, Phosphite ester, Potassium tert-butoxide, Prenylation, Propiolic acid, Protecting group, Pyridine, Pyridinium chlorochromate, Pyridinium p-toluenesulfonate, Rearrangement reaction, Ruthenium(III) chloride, Silyl ether, Sodium bis(trimethylsilyl)amide, Sodium borohydride, Sodium carbonate, Sodium iodide, Stanford University, Triazabicyclodecene, Trimethylsilyl chloride, Triphosgene, Verbenone, Walden inversion, Wittig reaction, Zinc chloride, 1,4-Dioxane, 2,6-Lutidine, 2-Methoxypropene, 4-Dimethylaminopyridine. Expand index (50 more) »

Acetate

An acetate is a salt formed by the combination of acetic acid with an alkaline, earthy, metallic or nonmetallic and other base.

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Acetic acid

Acetic acid, systematically named ethanoic acid, is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H or C2H4O2).

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Acetic anhydride

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O.

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Acetonide

In organic chemistry, an acetonide is the functional group composed of the cyclic ketal of a diol with acetone.

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Acyloin

Acyloins or α-hydroxy ketones are a class of organic compounds which all possess a hydroxy group adjacent to a ketone group.

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Alcohol

In chemistry, an alcohol is any organic compound in which the hydroxyl functional group (–OH) is bound to a carbon.

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Aldehyde

An aldehyde or alkanal is an organic compound containing a functional group with the structure −CHO, consisting of a carbonyl center (a carbon double-bonded to oxygen) with the carbon atom also bonded to hydrogen and to an R group, which is any generic alkyl or side chain.

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Aldol reaction

The aldol reaction is a means of forming carbon–carbon bonds in organic chemistry.

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Alkene

In organic chemistry, an alkene is an unsaturated hydrocarbon that contains at least one carbon–carbon double bond.

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Alkylation

Alkylation is the transfer of an alkyl group from one molecule to another.

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Alkyne

In organic chemistry, an alkyne is an unsaturated hydrocarbon containing at least one carbon—carbon triple bond.

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Allyl bromide

Allyl bromide (3-bromopropene) is an organic halide.

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Alpha-Pinene

α-Pinene is an organic compound of the terpene class, one of two isomers of pinene.

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Ammonium chloride

Ammonium chloride is an inorganic compound with the formula NH4Cl and a white crystalline salt that is highly soluble in water.

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Ammonium fluoride

Ammonium fluoride is the inorganic compound with the formula NH4F.

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Benzoic acid

Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and a simple aromatic carboxylic acid.

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Bromine

Bromine is a chemical element with symbol Br and atomic number 35.

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Carbonate ester

A carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid.

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Catalytic cycle

In chemistry, a catalytic cycle is a multistep reaction mechanism that involves a catalyst.

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Chemical trap

In chemistry, a chemical trap is a chemical compound that is used to detect a unstable chemical compounds.

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Chloroalkyl ether

Chloroalkyl ethers are a class of organic compounds with the general structure R-O-(CH2)n-Cl, characterized as an ether connected to a chloromethyl group via an alkane chain.

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Chrysanthenone

Chrysanthenone (C10H14O) is a terpene.

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Convergent synthesis

In chemistry a convergent synthesis is a strategy that aims to improve the efficiency of multistep synthesis, most often in organic synthesis.

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Crabtree's catalyst

Crabtree's catalyst is an organoiridium compound with the formula PF6.

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DABCO

DABCO (1,4-diazabicyclooctane) is an organic compound with the formula N2(C2H4)3.

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Danishefsky Taxol total synthesis

The Danishefsky Taxol total synthesis in organic chemistry is an important third Taxol synthesis published by the group of Samuel Danishefsky in 1996 two years after the first two efforts described in the Holton Taxol total synthesis and the Nicolaou Taxol total synthesis.

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Deprotonation

Deprotonation is the removal (transfer) of a proton (a hydrogen cation, H+) from a Brønsted–Lowry acid in an acid-base reaction.

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Dess–Martin periodinane

Dess–Martin periodinane (DMP) is a chemical reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.

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Diene

In organic chemistry a diene or diolefin is a hydrocarbon that contains two carbon double bonds.

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Diol

A diol or glycol is a chemical compound containing two hydroxyl groups (−OH groups).

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English Canada

English Canada is a term referring to one of the following.

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Epoxide

An epoxide is a cyclic ether with a three-atom ring.

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Eschenmoser's salt

Eschenmoser's salt, dimethylmethylideneammonium iodide, is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH2N(CH3)2.

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Ester

In chemistry, an ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH (hydroxyl) group is replaced by an –O–alkyl (alkoxy) group.

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Gilman reagent

A Gilman reagent is a lithium and copper (diorganocopper) reagent compound, R2CuLi, where R is an alkyl or aryl.

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Grignard reaction

The Grignard reaction (pronounced) is an organometallic chemical reaction in which alkyl, vinyl, or aryl-magnesium halides (Grignard reagents) add to a carbonyl group in an aldehyde or ketone.

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Grob fragmentation

In chemistry, a Grob fragmentation is an elimination reaction that breaks a neutral aliphatic chain into three fragments: a positive ion spanning atoms 1 and 2 (the "electrofuge"), an unsaturated neutral fragment spanning positions 3 and 4, and a negative ion (the "nucleofuge") comprising the rest of the chain.

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Holton Taxol total synthesis

The Holton Taxol total synthesis, published by Robert A. Holton and his group at Florida State University in 1994 was the first total synthesis of Taxol (generic name: paclitaxel).

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Homologous series

In organic chemistry, a homologous series is a series of compounds with the same functional group and similar chemical properties.

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Hydrochloric acid

Hydrochloric acid is a colorless inorganic chemical system with the formula.

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Hydrogen

Hydrogen is a chemical element with symbol H and atomic number 1.

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Imidazole

Imidazole is an organic compound with the formula C3N2H4.

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In situ

In situ (often not italicized in English) is a Latin phrase that translates literally to "on site" or "in position".

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Isomerization

In chemistry isomerization (also isomerisation) is the process by which one molecule is transformed into another molecule which has exactly the same atoms, but the atoms have a different arrangement e.g. A-B-C → B-A-C (these related molecules are known as isomers). In some molecules and under some conditions, isomerization occurs spontaneously.

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Journal of the American Chemical Society

The Journal of the American Chemical Society (also known as JACS) is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society.

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Ketone

In chemistry, a ketone (alkanone) is an organic compound with the structure RC(.

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Kuwajima Taxol total synthesis

The Kuwajima Taxol total synthesis by the group of Isao Kuwajima of the Tokyo Institute of Technology is one of several efforts in taxol total synthesis published in the 1990s.

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Lithium aluminium hydride

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula LiAlH4.

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Lithium bromide

Lithium bromide (LiBr) is a chemical compound of lithium and bromine.

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Lithium diisopropylamide

Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula 2NLi.

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Mesylate

In chemistry, a mesylate is any salt or ester of methanesulfonic acid (CH3SO3H).

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Meta-Chloroperoxybenzoic acid

meta-Chloroperoxybenzoic acid (mCPBA) is a peroxycarboxylic acid used widely as an oxidant in organic synthesis.

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Methanesulfonyl chloride

Methanesulfonyl chloride (mesyl chloride) is an organosulfur compound with the formula CH3SO2Cl.

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Methanol

Methanol, also known as methyl alcohol among others, is a chemical with the formula CH3OH (a methyl group linked to a hydroxyl group, often abbreviated MeOH).

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Methoxymethylenetriphenylphosphine

Methoxymethylenetriphenylphosphine is a Wittig reagent with used as an reagent in the homologization of aldehydes and ketones to extended aldehydes, an organic reaction first reported in 1958.

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Methylene group

In organic chemistry, a methylene group is any part of a molecule that consists of two hydrogen atoms bound to a carbon atom, which is connected to the remainder of the molecule by a double bond.

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Mukaiyama Taxol total synthesis

The Mukaiyama taxol total synthesis published by the group of Teruaki Mukaiyama of the Tokyo University of Science between 1997 and 1999 was the 6th successful taxol total synthesis.

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N,N-Diisopropylethylamine

N,N-Diisopropylethylamine, or Hünig's base, DIPEA or DIEA, is an organic compound and an amine.

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N-Methylmorpholine N-oxide

N-Methylmorpholine N-oxide (more correctly 4-methylmorpholine 4-oxide), NMO or NMMO is an organic compound.

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Nicolaou Taxol total synthesis

The Nicolaou Taxol total synthesis, published by K. C. Nicolaou and his group in 1994 concerns the total synthesis of Taxol.

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Nucleophilic addition

In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electron-deficient or electrophilic double or triple bond, a π bond, reacts with electron-rich reactant, termed a nucleophile, with disappearance of the double bond and creation of two new single, or σ, bonds.

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Nucleophilic conjugate addition

Nucleophilic conjugate addition is a type of organic reaction.

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Nucleophilic substitution

In organic and inorganic chemistry, nucleophilic substitution is a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive charge of an atom or a group of atoms to replace a leaving group; the positive or partially positive atom is referred to as an electrophile.

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Ojima lactam

The Ojima lactam is an organic compound of some importance in the commercial production of Taxol.

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Organic chemistry

Organic chemistry is a chemistry subdiscipline involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.

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Organic redox reaction

Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds.

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Osmium tetroxide

Osmium tetroxide (also osmium(VIII) oxide) is the chemical compound with the formula OsO4.

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Oxaziridine

An oxaziridine is an organic molecule that features a three-membered heterocycle containing oxygen, nitrogen, and carbon.

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Oxetane

Oxetane, or 1,3-propylene oxide, is an heterocyclic organic compound with the molecular formula, having a four-membered ring with three carbon atoms and one oxygen atom.

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Ozonolysis

Ozonolysis is an organic reaction where the unsaturated bonds of alkenes, alkynes, or azo compounds are cleaved with ozone.

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Paclitaxel total synthesis

Paclitaxel total synthesis in organic chemistry is a major ongoing research effort in the total synthesis of paclitaxel (Taxol).

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Paul Wender

Paul A. Wender is an American chemist, focusing in organic chemistry, organometallic chemistry, synthesis, catalysis, chemical biology, imaging, drug delivery, molecular therapeutics, currently the Francis W. Bergstrom Professor of Chemistry at Stanford University and is an Elected Fellow at the American Association for the Advancement of Science, American Academy of Arts and Sciences.

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Phenyllithium

Phenyllithium or lithobenzene is an organometallic agent with the empirical formula C6H5Li.

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Phosphite ester

In chemistry a phosphite ester or organophosphite usually refers to an organophosphorous compound with the formula P(OR)3.

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Potassium tert-butoxide

Potassium tert-butoxide is the chemical compound with the formula K+(CH3)3CO−.

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Prenylation

Prenylation (also known as isoprenylation or lipidation) is the addition of hydrophobic molecules to a protein or chemical compound.

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Propiolic acid

Propiolic acid is the organic compound with the formula HC2CO2H.

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Protecting group

A protecting group or protective group is introduced into a molecule by chemical modification of a functional group to obtain chemoselectivity in a subsequent chemical reaction.

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Pyridine

Pyridine is a basic heterocyclic organic compound with the chemical formula C5H5N.

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Pyridinium chlorochromate

Pyridinium chlorochromate (PCC) is a yellow-orange salt with the formula.

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Pyridinium p-toluenesulfonate

Pyridinium p-toluenesulfonate (PPTS) is a salt of pyridine and ''p''-toluenesulfonic acid.

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Rearrangement reaction

A rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule.

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Ruthenium(III) chloride

Ruthenium(III) chloride is the chemical compound with the formula RuCl3.

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Silyl ether

Silyl ethers are a group of chemical compounds which contain a silicon atom covalently bonded to an alkoxy group.

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Sodium bis(trimethylsilyl)amide

Sodium bis(trimethylsilyl)amide is the organosilicon compound with the formula ((CH3)3Si)2NNa. This species, usually called NaHMDS (sodium hexamethyldisilazide), is a strong base used for deprotonation reactions or base-catalyzed reactions. Its advantages are that it is commercially available as a solid and it is soluble not only in ethers, such as THF or diethyl ether, but also in aromatic solvents, like benzene and toluene by virtue of the lipophilic TMS groups. NaHMDS is quickly destroyed by water to form sodium hydroxide and bis(trimethylsilyl)amine.

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Sodium borohydride

Sodium borohydride, also known as sodium tetrahydridoborate and sodium tetrahydroborate, is an inorganic compound with the formula NaBH4.

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Sodium carbonate

Sodium carbonate, Na2CO3, (also known as washing soda, soda ash and soda crystals, and in the monohydrate form as crystal carbonate) is the water-soluble sodium salt of carbonic acid.

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Sodium iodide

Sodium iodide (chemical formula NaI) is an ionic compound formed from the chemical reaction of sodium metal and iodine.

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Stanford University

Stanford University (officially Leland Stanford Junior University, colloquially the Farm) is a private research university in Stanford, California.

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Triazabicyclodecene

No description.

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Trimethylsilyl chloride

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl.

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Triphosgene

Triphosgene (bis(trichloromethyl) carbonate (BTC), C3Cl6O3) is a chemical compound that is used as a safer substitute for phosgene, because, at room temperature, it is a solid crystal, as opposed to phosgene, which is a gas.

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Verbenone

Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants.

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Walden inversion

Walden inversion is the inversion of a chiral center in a molecule in a chemical reaction.

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Wittig reaction

The Wittig reaction or Wittig olefination is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide (often called a Wittig reagent) to give an alkene and triphenylphosphine oxide.

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Zinc chloride

Zinc chloride is the name of chemical compounds with the formula ZnCl2 and its hydrates.

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1,4-Dioxane

1,4-Dioxane is a heterocyclic organic compound, classified as an ether.

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2,6-Lutidine

2,6-Lutidine is a natural heterocyclic aromatic organic compound with the formula (CH3)2C5H3N.

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2-Methoxypropene

2-Methoxypropene is an ether with the chemical formula C4H8O.

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4-Dimethylaminopyridine

4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH3)2NC5H4N.

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References

[1] https://en.wikipedia.org/wiki/Wender_Taxol_total_synthesis

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