Economical route for oxidative cleavage of double bond to synthesize taxol side chain

Sumati Bhatia; Sukhdev Singh; Rajesh Kumar; Amit Kumar; Carl Erik Olsen; Ashok K. Prasad

Economical route for oxidative cleavage of double bond to synthesize taxol side chain

Sumati Bhatia, Sukhdev Singh, Rajesh Kumar, Amit Kumar, Carl Erik Olsen, Ashok K. Prasad

Section for Plant Biochemistry

5 Citations (Scopus)

Abstract

An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2- hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1′-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide using KMnO₄-NaIO₄-K₂CO₃ as oxidant in acetone-water in much higher yields of 80% than the conventional RuCl ₃-NaIO₄ method. Further, the developed methodology has been successfully used for the synthesis of O-acetylated taxotere side chain (2R,3S)-2-acetoxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid and taxol side chain analogues (2R,3S)- 2-acetoxy-3-(4″-chloro-/4″- fluoro-/4″-trifluoromethyl-benzamido)-3-phenylpropanoic acid from their corresponding alkene precursor, which demonstrate the generality of the developed oxidative cleavage methodology.

Original language	English
Journal	Indian Journal of Chemistry. Section B
Volume	52B
Issue number	03
Pages (from-to)	379-386
Number of pages	8
ISSN	0376-4699
Publication status	Published - Mar 2013

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@article{1512167249fa4ad6b8c00567ebadebaa,

title = "Economical route for oxidative cleavage of double bond to synthesize taxol side chain",

abstract = "An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2- hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1′-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide using KMnO4-NaIO4-K2CO3 as oxidant in acetone-water in much higher yields of 80% than the conventional RuCl 3-NaIO4 method. Further, the developed methodology has been successfully used for the synthesis of O-acetylated taxotere side chain (2R,3S)-2-acetoxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid and taxol side chain analogues (2R,3S)- 2-acetoxy-3-(4″-chloro-/4″- fluoro-/4″-trifluoromethyl-benzamido)-3-phenylpropanoic acid from their corresponding alkene precursor, which demonstrate the generality of the developed oxidative cleavage methodology.",

author = "Sumati Bhatia and Sukhdev Singh and Rajesh Kumar and Amit Kumar and Olsen, {Carl Erik} and Prasad, {Ashok K.}",

year = "2013",

month = mar,

language = "English",

volume = "52B",

pages = "379--386",

journal = "Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry",

issn = "0376-4699",

publisher = "CSIR-NISCAIR! ",

number = "03",

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TY - JOUR

T1 - Economical route for oxidative cleavage of double bond to synthesize taxol side chain

AU - Bhatia, Sumati

AU - Singh, Sukhdev

AU - Kumar, Rajesh

AU - Kumar, Amit

AU - Olsen, Carl Erik

AU - Prasad, Ashok K.

PY - 2013/3

Y1 - 2013/3

N2 - An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2- hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1′-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide using KMnO4-NaIO4-K2CO3 as oxidant in acetone-water in much higher yields of 80% than the conventional RuCl 3-NaIO4 method. Further, the developed methodology has been successfully used for the synthesis of O-acetylated taxotere side chain (2R,3S)-2-acetoxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid and taxol side chain analogues (2R,3S)- 2-acetoxy-3-(4″-chloro-/4″- fluoro-/4″-trifluoromethyl-benzamido)-3-phenylpropanoic acid from their corresponding alkene precursor, which demonstrate the generality of the developed oxidative cleavage methodology.

AB - An efficient, economical and industry-friendly methodology has been developed for the synthesis of C-13 side chain of taxol, (2R,3S)-3-benzamido-2- hydroxy-3-phenylpropanoic acid by oxidative cleavage of alkene precursor N-[(1S,2S)-2-(1′-ethoxyethoxy)-1-phenylbut-3-en-1-yl]benzamide using KMnO4-NaIO4-K2CO3 as oxidant in acetone-water in much higher yields of 80% than the conventional RuCl 3-NaIO4 method. Further, the developed methodology has been successfully used for the synthesis of O-acetylated taxotere side chain (2R,3S)-2-acetoxy-3-[N-(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid and taxol side chain analogues (2R,3S)- 2-acetoxy-3-(4″-chloro-/4″- fluoro-/4″-trifluoromethyl-benzamido)-3-phenylpropanoic acid from their corresponding alkene precursor, which demonstrate the generality of the developed oxidative cleavage methodology.

M3 - Journal article

SN - 0376-4699

VL - 52B

SP - 379

EP - 386

JO - Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

JF - Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry

IS - 03

ER -

Economical route for oxidative cleavage of double bond to synthesize taxol side chain

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