American Chemical Society
jo1c02634_si_001.pdf (5.99 MB)

Enantiospecific Total Synthesis and Absolute Configuration Assignment of Chabrolobenzoquinone H

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journal contribution
posted 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.