Artman Gerald D, Grubbs Alan W, Williams Robert M
Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
J Am Chem Soc. 2007 May 16;129(19):6336-42. doi: 10.1021/ja070259i. Epub 2007 Apr 25.
Concise asymmetric total syntheses of the fungal metabolites (-)-stephacidin A, (+)-stephacidin B, and (+)-notoamide B are described. Key features of these total syntheses include (1) a facile synthesis of (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 form the [2.2.2] bridged bicyclic ring system. Furthermore, our synthesis has taken advantage of microwave heating to shorten reaction times as well as increase yields for the preparation of vital intermediates.
本文描述了真菌代谢产物(-)-斯蒂芬酸A、(+)-斯蒂芬酸B和(+)-诺托酰胺B的简洁不对称全合成。这些全合成的关键特征包括:(1)(R)-烯丙基脯氨酸甲酯的简便合成;(2)通往吡喃吲哚环系统的改进路线;(3)引入重要官能团的新型交叉复分解策略;(4)通过SN2'环化形成[2.2.2]桥连双环系统。此外,我们的合成利用微波加热来缩短反应时间,并提高制备关键中间体的产率。