Convergent Total Synthesis of (–)-Principinol D, a Rearranged Kaurane Diterpenoid

20 March 2019, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

The total synthesis of principinol D, a rearranged kaurane diterpenoid, is reported. This grayanane natural product was constructed via a convergent fragment coupling approach, wherein the central 7-membered ring was synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction, followed by a diastereoselective SmI2-mediated ketone reduction. The convergent strategy reported herein may be an entry point to a wide range of kaurane diterpenoids.

Keywords

total synthesis
terpenoid
Natural Product

Supplementary materials

Title
Description
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Title
Compound 2
Description
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Title
Principinol D - SI
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