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

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

240 Scopus citations

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 (US)
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
State	Published - Jan 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
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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year = "1995",

month = jan,

doi = "10.1021/ja00107a007",

language = "English (US)",

volume = "117",

pages = "634--644",

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AU - Nicolaou, K. C.

AU - Liu, J. J.

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

Y1 - 1995/1

N2 - 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.

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

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