Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
J Am Chem Soc. 2016 Aug 3;138(30):9425-8. doi: 10.1021/jacs.6b06623. Epub 2016 Jul 26.
An expedient, practical, and enantioselective route to the highly congested ent-kaurane diterpene maoecrystal V is presented. This route, which has been several years in the making, is loosely modeled after a key pinacol shift in the proposed biosynthesis. Only 11 steps, many of which are strategic in that they build key skeletal bonds and incorporate critical functionalities, are required to access (-)-maoecrystal V. Several unique and unexpected maneuvers are featured in this potentially scalable pathway. Reevaluation of the biological activity calls into question the initial exuberance surrounding this natural product.
本文介绍了一种简便、实用且对映选择性的方法，用于合成高度稠合的-ent-贝壳杉烷二萜maoecrystal V。这条路线历经多年的研究，大致模拟了提议的生物合成中的一个关键频哪醇重排。仅需 11 步（其中许多步都是策略性的，因为它们构建了关键的骨架键并引入了关键的官能团），即可获得（-）-maoecrystal V。这条具有潜在可扩展性的途径具有几个独特且出乎意料的操作。对生物活性的重新评估使人们对这种天然产物的最初热情产生了质疑。
