The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-epoxypaclitaxel

Geraldine C.B. Harriman; Ravi K. Jalluri; Gary L. Granewald; David G. Vander Velde; Gunda I. Georg; Richard H. Himes

doi:10.1016/0040-4039(95)01928-B

The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-epoxypaclitaxel

Geraldine C.B. Harriman
, Ravi K. Jalluri
, Gary L. Granewald
, David G. Vander Velde
, Gunda I. Georg
, Richard H. Himes

Medicinal Chemistry

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

12 Scopus citations

Abstract

Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to play a role in the stereoselectivity of the reaction as epoxidation occurred at the β-face of the molecule. 10-Deacetoxy-11,12-epoxypaclitaxel (10) proved to be more active than paclitaxel (1) in the microtubule assembly assay and three-fold less cytotoxic than paclitaxel against B16 melanoma cells.

Original language	English (US)
Pages (from-to)	8909-8912
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	49
DOIs	https://doi.org/10.1016/0040-4039(95)01928-B
State	Published - Dec 4 1995

Bibliographical note

Funding Information:
The authors wish to thank the National Cancer Institute for financial paclitaxel for these studies.

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title = "The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-epoxypaclitaxel",

abstract = "Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to play a role in the stereoselectivity of the reaction as epoxidation occurred at the β-face of the molecule. 10-Deacetoxy-11,12-epoxypaclitaxel (10) proved to be more active than paclitaxel (1) in the microtubule assembly assay and three-fold less cytotoxic than paclitaxel against B16 melanoma cells.",

author = "Harriman, \{Geraldine C.B.\} and Jalluri, \{Ravi K.\} and Granewald, \{Gary L.\} and \{Vander Velde\}, \{David G.\} and Georg, \{Gunda I.\} and Himes, \{Richard H.\}",

note = "Funding Information: The authors wish to thank the National Cancer Institute for financial paclitaxel for these studies.",

year = "1995",

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doi = "10.1016/0040-4039(95)01928-B",

language = "English (US)",

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journal = "Tetrahedron Letters",

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T1 - The chemistry of the taxane diterpene

T2 - Stereoselective synthesis of 10-deacetoxy-11,12-epoxypaclitaxel

AU - Harriman, Geraldine C.B.

AU - Jalluri, Ravi K.

AU - Granewald, Gary L.

AU - Vander Velde, David G.

AU - Georg, Gunda I.

AU - Himes, Richard H.

N1 - Funding Information: The authors wish to thank the National Cancer Institute for financial paclitaxel for these studies.

PY - 1995/12/4

Y1 - 1995/12/4

N2 - Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to play a role in the stereoselectivity of the reaction as epoxidation occurred at the β-face of the molecule. 10-Deacetoxy-11,12-epoxypaclitaxel (10) proved to be more active than paclitaxel (1) in the microtubule assembly assay and three-fold less cytotoxic than paclitaxel against B16 melanoma cells.

AB - Epoxidation of the olefin in 10-deacetoxybaccatin III (6) and 10-deacetoxypaclitaxel (9) was accomplished with meta-chloroperbenzoic acid leading to a novel pentacyclic ring system. Hydroxyl directed delivery of the epoxidizing agent did not appear to play a role in the stereoselectivity of the reaction as epoxidation occurred at the β-face of the molecule. 10-Deacetoxy-11,12-epoxypaclitaxel (10) proved to be more active than paclitaxel (1) in the microtubule assembly assay and three-fold less cytotoxic than paclitaxel against B16 melanoma cells.

UR - https://www.scopus.com/pages/publications/0028863301

UR - https://www.scopus.com/pages/publications/0028863301#tab=citedBy

U2 - 10.1016/0040-4039(95)01928-B

DO - 10.1016/0040-4039(95)01928-B

M3 - Article

AN - SCOPUS:0028863301

SN - 0040-4039

VL - 36

SP - 8909

EP - 8912

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 49

ER -

The chemistry of the taxane diterpene: Stereoselective synthesis of 10-deacetoxy-11,12-epoxypaclitaxel

Abstract

Bibliographical note

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