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16-Step Synthesis of the Isoryanodane Diterpene (+)-Perseanol

preprint
submitted on 20.05.2019 and posted on 21.05.2019 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.

Funding

NIGMS RGM097582-01

R35GM118191-01

5T32GM007616-37

1F31GM120821

History

Email Address of Submitting Author

reisman@caltech.edu

Institution

California Institute of Technology

Country

USA

ORCID For Submitting Author

0000-0001-8244-9300

Declaration of Conflict of Interest

No conflict of Interest

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