Convergent Total Synthesis of Principinol D, a Rearranged Kaurane Diterpenoid.

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 seven-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.

SUBMITTER: Turlik A 

PROVIDER: S-EPMC7192013 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature