11-Step Total Synthesis of (-)-Maoecrystal V.
11-Step Total Synthesis of (-)-Maoecrystal V.
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DOI：
10.1021/jacs.6b06623
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发表时间：
2016-08-03
影响因子：
15
通讯作者：
Baran PS
中科院分区：
文献类型：
--
作者：
Cernijenko A;Risgaard R;Baran PS
给出了一条简便、实用、对映体选择性好的合成高稠度对映异构烷二萜毛晶V的路线。这条路线已经酝酿了几年，是在拟议的生物合成中的一个关键的Pinacol转变之后松散地模仿的。访问(−)-毛晶体V只需要11个步骤，其中许多步骤具有战略意义，因为它们建立了关键的骨架键并包含了关键功能。在这条潜在的可扩展路径中，有几个独特和意想不到的操作。对生物活性的重新评估使人们对这种天然产品最初的热情产生了疑问。
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.