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

Abstract

Our 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.

Key words

dysideanone B - dysiherbol A - meroterpenoid - natural product - structure revision - total synthesis

Publication History

Received: 28 June 2021

Accepted after revision: 08 July 2021

Accepted Manuscript online:
08 July 2021

Article published online:
23 July 2021

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