Total Synthesis of Vinigrol

The longstanding challenge posed by the complex diterpene vinigrol has been answered for the first time. The notorious difficulty in synthesizing vinigrol stems from its unprecedented decahydro-1,5-butanonaphthalene ring system, eight contiguous stereocenters, and highly congested functionality. This Communication delineates a stereocontrolled 23-step route to vinigrol that is scalable (>5 g prepared of a late-stage intermediate), minimally reliant on protecting group chemistry, and facilitated by a number of unique and chemoselective transformations.长期以来，复杂二萜类化合物维尼格醇（vinigrol）所带来的合成难题首次得到破解。维尼格醇的合成极具挑战性，这一公认的难点源于其前所未有的十氢-1,5-丁并萘环系、八个连续手性中心以及高度拥挤的官能团排布。本通讯详述了一条立体可控的23步维尼格醇合成路线，该路线可实现规模化放大（已制备得到超过5克的后期中间体），对保护基策略的依赖度极低，并通过一系列独特且具有化学选择性的转化反应得以完成。