Synthetic studies on taxol: Highly stereoselective construction of the taxol C-ring via SN2′ reduction of an allylic phosphonium salt

Masayuki Utsugi; Masayuki Miyano; Masahisa Nakada

doi:10.1021/ol0608606

Synthetic studies on taxol: Highly stereoselective construction of the taxol C-ring via S_N2′ reduction of an allylic phosphonium salt

Masayuki Utsugi, Masayuki Miyano, Masahisa Nakada^*

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereoselective S _N2′ reduction of the allylic phosphonium salts.

Original language	English
Pages (from-to)	2973-2976
Number of pages	4
Journal	Organic Letters
Volume	8
Issue number	14
DOIs	https://doi.org/10.1021/ol0608606
Publication status	Published - 2006 Jul 6

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereoselective S N2′ reduction of the allylic phosphonium salts.",

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AB - The highly stereoselective construction of the C3 stereogenic center of the taxol C-ring is described. The trans isomer at the C3-C8 position of the taxol C-ring, which is required for the total synthesis, as well as its diastereomeric cis isomer were successfully synthesized with highly diastereoselective S N2′ reduction of the allylic phosphonium salts.

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Synthetic studies on taxol: Highly stereoselective construction of the taxol C-ring via S_N2′ reduction of an allylic phosphonium salt

Abstract

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