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Download fileEnantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H
journal contribution
posted on 2021-12-22, 17:37 authored by Stergios
R. Rizos, Konstantinos A. Ouzounthanasis, Alexandros E. KoumbisChabrolobenzoquinone 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.
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targeted natural productstereospecific olefin crossmetathesis reaction followedmalonic ester synthesisenantiospecific total synthesisbenzoquinone aldehyde partnerabsolute configuration assignmentabsolute configurationsynthesized viastille couplingmeroditerpene metabolitekrapcho decarboxylationcytotoxic activity