Total Synthesis of Taxol. 2. Construction of A and C Ring Intermediates and Initial Attempts To Construct the ABC Ring System

K. C. Nicolaou; J. J. Liu; Z. Yang; H. Ueno; E. J. Sorensen; C. F. Claiborne; R. K. Guy; C. K. Hwang; M. Nakada; P. G. Nantermet

doi:10.1021/ja00107a007

Total Synthesis of Taxol. 2. Construction of A and C Ring Intermediates and Initial Attempts To Construct the ABC Ring System

K. C. Nicolaou^*, J. J. Liu, Z. Yang, H. Ueno, E. J. Sorensen, C. F. Claiborne, R. K. Guy, C. K. Hwang, M. Nakada, P. G. Nantermet

^*Corresponding author for this work

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

228 Citations (Scopus)

Abstract

A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro—McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A—B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

Original language	English
Pages (from-to)	634-644
Number of pages	11
Journal	Journal of the American Chemical Society
Volume	117
Issue number	2
DOIs	https://doi.org/10.1021/ja00107a007
Publication status	Published - 1995 Jan
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja00107a007

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Nicolaou, K. C., Liu, J. J., Yang, Z., Ueno, H., Sorensen, E. J., Claiborne, C. F., Guy, R. K., Hwang, C. K., Nakada, M., & Nantermet, P. G. (1995). Total Synthesis of Taxol. 2. Construction of A and C Ring Intermediates and Initial Attempts To Construct the ABC Ring System. Journal of the American Chemical Society, 117(2), 634-644. https://doi.org/10.1021/ja00107a007

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abstract = "A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro—McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A—B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.",

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AU - Yang, Z.

AU - Ueno, H.

AU - Sorensen, E. J.

AU - Claiborne, C. F.

AU - Guy, R. K.

AU - Hwang, C. K.

AU - Nakada, M.

AU - Nantermet, P. G.

PY - 1995/1

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AB - A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro—McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A—B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

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Total Synthesis of Taxol. 2. Construction of A and C Ring Intermediates and Initial Attempts To Construct the ABC Ring System

Abstract

ASJC Scopus subject areas

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