Bioinspired Total Synthesis of Marine Anticancer Meroterpenoids Dysideanone B and Dysiherbol A and Structure Revision of Dysiherbol A

Author:

Lu ZhaoyongORCID,Chong Chuanke

Abstract

AbstractOur recent progress on the total synthesis of marine anticancer sesquiterpene quinone/hydroquinone dysideanone B and dysiherbol A is briefly highlighted. This success relied on some key transformations. The union of the terpene and quinone/hydroquinone moieties was realized through a site and stereoselective α-position alkylation of Wieland–Miescher ketone derivative with a bulky benzyl bromide. The 6/6/6/6-tetracycle of dysideanone B was constructed using an intramolecular radical cyclization and the 6/6/5/6-fused core structure of dysiherbol A was forged by an intramolecular Heck reaction, respectively. The possible origin of ethoxy group in dysideanone B was revealed by mimicking the isolation conditions at a late stage. The structure of dysiherbol A was revised through the total synthesis of this natural product. Schmalz’s synthesis of dysiherbol A was also included.

Funder

State Key Laboratory of Natural Medicines

National Natural Science Foundation of China

Fundamental Research Funds for the Central Universities

Fundamental Research Funds for the Central Universities, Nankai University

State Key Laboratory of Medicinal Chemical Biology

Nankai University

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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