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

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

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