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

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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.",

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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.

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Y1 - 1995/12/4

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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.

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ER -

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

Abstract

Bibliographical note

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