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

241 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
Biochemistry
General Chemistry
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",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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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.

UR - https://www.scopus.com/pages/publications/0028792481

UR - https://www.scopus.com/pages/publications/0028792481#tab=citedBy

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 2

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

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