Total Synthesis of Taxol. 3. Formation of Taxol's ABC Ring Skeleton

K. C. Nicolaou; Z. Yang; J. J. Liu; P. G. Nantermet; C. F. Claiborne; J. Renaud; R. K. Guy; K. Shibayama

doi:10.1021/ja00107a008

Total Synthesis of Taxol. 3. Formation of Taxol's ABC Ring Skeleton

K. C. Nicolaou
, Z. Yang
, J. J. Liu
, P. G. Nantermet
, C. F. Claiborne
, J. Renaud
, R. K. Guy
, K. Shibayama

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

186 Scopus citations

Abstract

The synthesis of Taxol's ABC ring system has been achieved. The Shapiro coupling of an aldehydic C ring synthon (8) with an anionic A ring synthon derived from hydrazone 9 gave, diastereoselectively, A-B conjugate 10. Functional group manipulations and McMurry ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMurry reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the C9,C10-diol (±)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.

Original language	English
Pages (from-to)	645-652
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	117
Issue number	2
DOIs	https://doi.org/10.1021/ja00107a008
State	Published - Jan 1995

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Total Synthesis of Taxol. 3. Formation of Taxol's ABC Ring Skeleton",

abstract = "The synthesis of Taxol's ABC ring system has been achieved. The Shapiro coupling of an aldehydic C ring synthon (8) with an anionic A ring synthon derived from hydrazone 9 gave, diastereoselectively, A-B conjugate 10. Functional group manipulations and McMurry ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMurry reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the C9,C10-diol (±)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.",

author = "Nicolaou, \{K. C.\} and Z. Yang and Liu, \{J. J.\} and Nantermet, \{P. G.\} and Claiborne, \{C. F.\} and J. Renaud and Guy, \{R. K.\} and K. Shibayama",

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language = "English",

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T1 - Total Synthesis of Taxol. 3. Formation of Taxol's ABC Ring Skeleton

AU - Nicolaou, K. C.

AU - Yang, Z.

AU - Liu, J. J.

AU - Nantermet, P. G.

AU - Claiborne, C. F.

AU - Renaud, J.

AU - Guy, R. K.

AU - Shibayama, K.

PY - 1995/1

Y1 - 1995/1

N2 - The synthesis of Taxol's ABC ring system has been achieved. The Shapiro coupling of an aldehydic C ring synthon (8) with an anionic A ring synthon derived from hydrazone 9 gave, diastereoselectively, A-B conjugate 10. Functional group manipulations and McMurry ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMurry reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the C9,C10-diol (±)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.

AB - The synthesis of Taxol's ABC ring system has been achieved. The Shapiro coupling of an aldehydic C ring synthon (8) with an anionic A ring synthon derived from hydrazone 9 gave, diastereoselectively, A-B conjugate 10. Functional group manipulations and McMurry ring closure produced the highly functionalized ABC ring system 17. Extensive attempts to optimize the McMurry reaction revealed a single predominant side reaction leading to byproducts 19 and 20. Resolution of the C9,C10-diol (±)-17 via its camphanyl esters provided the ABC ring system as its natural isomer (+)17.

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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. 3. Formation of Taxol's ABC Ring Skeleton

Abstract

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