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16-Step Synthesis of the Isoryanodane Diterpene (+)-Perseanol
preprintsubmitted on 20.05.2019, 15:59 and posted on 21.05.2019, 15:21 by Arthur Han, Yujia Tao, Sarah Reisman
(+)-Perseanol is an isoryanodane diterpene with potent antifeedant and insecticidal properties isolated from the tropical shrub Persea indica. Here we report the first chemical synthesis of (+)-perseanol, which proceeds in 16 steps from commercially available (R)-pulegone. The synthesis features a two-step annulation process that rapidly assembles the tetracyclic core from readily accessible cyclopentyl building blocks. This work demonstrates how convergent fragment coupling, when combined with strategic oxidation tactics, can enable the concise synthesis of complex and highly oxidized diterpene natural products.
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