Smith Amos B, Davulcu Akin H, Cho Young Shin, Ohmoto Kazuyuki, Kürti László, Ishiyama Haruaki
Department of Chemistry, Monell Chemical Senses Center and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA.
J Org Chem. 2007 Jun 22;72(13):4596-610. doi: 10.1021/jo062422i. Epub 2007 May 19.
A first-generation strategy for construction of (+)-nodulisporic acids A (1) and B (2) is described. The strategy entails union of the eastern and western hemisphere subtargets via the indole synthesis protocol developed in our laboratory. Subsequent elaboration of rings E and F, however, revealed the considerable acid instability of the C(24) hydroxyl, thereby preventing further advancement. Nonetheless, preparation of the heptacyclic core of (+)-nodulisporic acids A and B, the total synthesis of (+)-nodulisporic acid F, the simplest member of the nodulisporic acid family, and elaboration of the heptacyclic core of (-)-nodulisporic acid D were achieved.
描述了一种构建（+）-节球孢菌素A（1）和B（2）的第一代策略。该策略需要通过我们实验室开发的吲哚合成方案将东半球和西半球的亚目标结合起来。然而，随后对E环和F环的修饰表明C（24）羟基具有相当大的酸不稳定性，从而阻碍了进一步的进展。尽管如此，仍实现了（+）-节球孢菌素A和B的七环核心的制备、（+）-节球孢菌素F（节球孢菌素家族中最简单的成员）的全合成以及（-）-节球孢菌素D的七环核心的修饰。
