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Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H
journal contributionposted on 2021-12-22, 17:37 authored by Stergios R. Rizos, Konstantinos A. Ouzounthanasis, Alexandros E. Koumbis
Chabrolobenzoquinone H (1), a meroditerpene metabolite with cytotoxic activity, is synthesized via a stereoselective Julia–Kocienski olefination between a chiral pool derived aliphatic PT-sulfone and a benzoquinone aldehyde partner. The latter was obtained via consecutive chain extension steps involving a Stille coupling and a stereospecific olefin cross-metathesis reaction followed by malonic ester synthesis and a Krapcho decarboxylation. Furthermore, this total synthesis securely determined the absolute configuration of the targeted natural product.
targeted natural productstereospecific olefin crossmetathesis reaction followedmalonic ester synthesisenantiospecific total synthesisbenzoquinone aldehyde partnerabsolute configuration assignmentabsolute configurationsynthesized viastille couplingmeroditerpene metabolitekrapcho decarboxylationcytotoxic activity