Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)-Taxusin and (-)-Taxol

Isao Kuwajima; Hiroyuki Kusama

doi:10.1055/s-2000-7619

Synlett 2000; 2000(10): 1385-1401
DOI: 10.1055/s-2000-7619

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Synthetic Studies on Taxoids: Enantioselective Total Synthesis of (+)-Taxusin and (-)-Taxol

Isao Kuwajima^* , Hiroyuki Kusama

^*The Kitasato Institute, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8642, Japan; Fax + 81 (3) 57 91 61 20; E-mail: kuwajima-i@kitasato.or.jp

Abstract

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To construct taxane ABC tricarbocycles, a useful methodology including an aldol-like eight-membered B ring cyclization between dienol silyl ethers and acetals was explored. By applying this methodology, the enantioselective total syntheses of (+)-taxusin and (-)-taxol have been achieved, starting from the substrate containing a chiral center at each C1 site, based on AC to ABC strategies. Syntheses of several artificial taxoids are also described.

total synthesis - terpenoids - cyclizations - stereoselective synthesis - asymmetric synthesis

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