Synthesis of the CD ring in taxol from (S)-(+)-carvone

Tony K.M. Shing; Chi M. Lee; Ho Y. Lo

doi:10.1016/S0040-4039(01)01802-0

Synthesis of the CD ring in taxol from (S)-(+)-carvone

Tony K.M. Shing, Chi M. Lee, Ho Y. Lo

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

Abstract

The tricycle 16 containing a functionalized CD ring is constructed from (S)-(+)-carvone in 21 steps involving a Baeyer-Villiger oxidation, an Oppenaurer oxidation and Meerwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, and an intramolecular S_N2 reaction as the key steps.

Original language	English
Pages (from-to)	8361-8363
Number of pages	3
Journal	Tetrahedron Letters
Volume	42
Issue number	47
DOIs	https://doi.org/10.1016/S0040-4039(01)01802-0
Publication status	Published - 2001 Nov 19
Externally published	Yes

Keywords

Baeyer-Villiger reactions
Grignard reactions
Hydroxylation
Taxoids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(01)01802-0

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title = "Synthesis of the CD ring in taxol from (S)-(+)-carvone",

abstract = "The tricycle 16 containing a functionalized CD ring is constructed from (S)-(+)-carvone in 21 steps involving a Baeyer-Villiger oxidation, an Oppenaurer oxidation and Meerwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, and an intramolecular SN2 reaction as the key steps.",

keywords = "Baeyer-Villiger reactions, Grignard reactions, Hydroxylation, Taxoids",

author = "Shing, {Tony K.M.} and Lee, {Chi M.} and Lo, {Ho Y.}",

note = "Funding Information: Financial support from CUHK Direct Grant (account no. 2060181) is gratefully acknowledged. ",

year = "2001",

month = nov,

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doi = "10.1016/S0040-4039(01)01802-0",

language = "English",

volume = "42",

pages = "8361--8363",

journal = "Tetrahedron Letters",

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T1 - Synthesis of the CD ring in taxol from (S)-(+)-carvone

AU - Shing, Tony K.M.

AU - Lee, Chi M.

AU - Lo, Ho Y.

N1 - Funding Information: Financial support from CUHK Direct Grant (account no. 2060181) is gratefully acknowledged.

PY - 2001/11/19

Y1 - 2001/11/19

N2 - The tricycle 16 containing a functionalized CD ring is constructed from (S)-(+)-carvone in 21 steps involving a Baeyer-Villiger oxidation, an Oppenaurer oxidation and Meerwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, and an intramolecular SN2 reaction as the key steps.

AB - The tricycle 16 containing a functionalized CD ring is constructed from (S)-(+)-carvone in 21 steps involving a Baeyer-Villiger oxidation, an Oppenaurer oxidation and Meerwein-Ponndorf-Verley reduction, a stereospecific Grignard addition, and an intramolecular SN2 reaction as the key steps.

KW - Baeyer-Villiger reactions

KW - Grignard reactions

KW - Hydroxylation

KW - Taxoids

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U2 - 10.1016/S0040-4039(01)01802-0

DO - 10.1016/S0040-4039(01)01802-0

M3 - Article

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SN - 0040-4039

VL - 42

SP - 8361

EP - 8363

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Synthesis of the CD ring in taxol from (S)-(+)-carvone

Abstract

Keywords

ASJC Scopus subject areas

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