Concise, Asymmetric, Stereocontrolled Total Synthesis of Stephacidins A, B and Notoamide B
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- 作者：Gerald D. Artman III ; Alan W. Grubbs ; Robert M. Williams
- 刊名：Journal of the American Chemical Society
- 出版年：2007
- 出版时间：May 16, 2007
- 年：2007
- 卷：129
- 期：19
- 页码：6336 - 6342
- 全文大小：192K
- 年卷期：v.129,no.19(May 16, 2007)
- ISSN：1520-5126
文摘
Concise asymmetric total syntheses of the fungal metabolites (-)-stephacidin A, (+)-stephacidinB, and (+)-notoamide B are described. Key features of these total syntheses include (1) a facile synthesisof (R)-allyl proline methyl ester, (2) a revised route toward the pyranoindole ring system, (3) a novel cross-metathesis strategy for the introduction of important functional groups, and (4) an SN2' cyclization to formthe [2.2.2] bridged bicyclic ring system. Furthermore, our synthesis has taken advantage of microwaveheating to shorten reaction times as well as increase yields for the preparation of vital intermediates.