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Total synthesis of taxol
K. C. Nicolaou ,
Z. Yang ,
J. J. Liu ,
H. Ueno ,
P. G. Nantermet ,
R. K. Guy ,
C. F. Claiborne ,
J. Renaud ,
E. A. Couladouros ,
K. Paulvannan ,
E. J. Sorensen
February 1994
February 1994
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Abstract
Taxol, a substance originally isolated from the Pacific yew tree (Taxus brevifolia)
more than two decades ago, has recently been approved for the clinical treatment of
cancer patients. Hailed as having provided one of the most significant advances in
cancer therapy, this molecule exerts its anticancer activity by inhibiting mitosis
through enhancement of the polymerization of tubulin and consequent stabilization
of microtubules. The scarcity of taxol and the ecological impact of harvesting it
have prompted extension searches for alternative sources including semisynthesis,
cellular culture production and chemical synthesis. The latter has been attempted
for almost two decades, but these attempts have been thwarted by the magnitude of
the synthetic challenge. Here we report the total synthesis of taxol by a convergent
strategy, which opens a chemical pathway for the production of both the natural product
itself and a variety of designed taxoids.