Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid

08 April 2019, Version 4
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 is constructed via a convergent fragment coupling approach, wherein the central 7-membered ring is synthesized at a late stage. The bicyclo[3.2.1]octane fragment is accessed by a Ni-catalyzed α-vinylation reaction. Strategic reductions include a diastereoselective SmI2-mediated ketone reduction with PhSH and a new protocol for selective ester reduction in the presence of ketones. The convergent strategy reported herein may be an entry point to the larger class 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
Description
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