A synthetic approach toward taxol analogs: Studies on the construction of the CD ring

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

doi:10.1016/j.tet.2004.07.094

A synthetic approach toward taxol analogs: Studies on the construction of the CD ring

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

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

12 Citations (Scopus)

Abstract

Tricycle 6, containing the CD ring of taxol, is constructed from (S)-(+)-carvone in 21 steps involving a Diels-Alder reaction with isoprene, 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)	9179-9197
Number of pages	19
Journal	Tetrahedron
Volume	60
Issue number	41
DOIs	https://doi.org/10.1016/j.tet.2004.07.094
Publication status	Published - 2004 Oct 4
Externally published	Yes

Keywords

Diels-Alder reaction
Reduction
Taxol analog

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.07.094

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title = "A synthetic approach toward taxol analogs: Studies on the construction of the CD ring",

abstract = "Tricycle 6, containing the CD ring of taxol, is constructed from (S)-(+)-carvone in 21 steps involving a Diels-Alder reaction with isoprene, 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.",

keywords = "Diels-Alder reaction, Reduction, Taxol analog",

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

note = "Funding Information: Financial support from CUHK Direct Grant (account no. 2060203) is gratefully acknowledged.",

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T1 - A synthetic approach toward taxol analogs

T2 - Studies on the construction of the CD ring

AU - Shing, Tony K.M.

AU - Lee, Chi M.

AU - Lo, Ho Y.

N1 - Funding Information: Financial support from CUHK Direct Grant (account no. 2060203) is gratefully acknowledged.

PY - 2004/10/4

Y1 - 2004/10/4

N2 - Tricycle 6, containing the CD ring of taxol, is constructed from (S)-(+)-carvone in 21 steps involving a Diels-Alder reaction with isoprene, 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.

AB - Tricycle 6, containing the CD ring of taxol, is constructed from (S)-(+)-carvone in 21 steps involving a Diels-Alder reaction with isoprene, 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.

KW - Diels-Alder reaction

KW - Reduction

KW - Taxol analog

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JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

A synthetic approach toward taxol analogs: Studies on the construction of the CD ring

Abstract

Keywords

ASJC Scopus subject areas

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