Synlett 2024; 35(05): 582-585
DOI: 10.1055/a-2066-0860
cluster
Biomimetic Synthesis

Practical and Scalable Total Syntheses of (+)-Dysidavarones A–C

Yang Kuang
,
Le Chang
,
Bingjian Wang
,
Jingyi Kang
,
Chuanke Chong
,
Zhaoyong Lu
This work was financially supported by the National Natural Science Foundation of China (Nos. 22171146, 21971121, and 22188101 to Z.L.) and the China Postdoctoral Science Foundation (No. 2021M701775 to C.C.).


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Abstract

A practical and scalable enantioselective total syntheses of the marine anticancer sesquiterpene quinone meroterpenoids (+)-dysidavarones A–C has been accomplished. The central bridged bicyclo[3.3.1]nonane structure of dysidavarones was efficiently established by a one-pot intermolecular diastereoselective alkylation and intramolecular α-arylation of a Wieland–Miescher ketone derivative with a substituted benzylic bromide, without protection of the more-reactive C(4) carbonyl group. (+)-Dysidavarones A and ‘E’ were prepared on a 150-mg scale, demonstrating the efficiency and reliability of our synthetic route and providing sufficient amounts of the dysidavarones for further bioactivity evaluation.

Supporting Information



Publication History

Received: 28 February 2023

Accepted after revision: 30 March 2023

Accepted Manuscript online:
30 March 2023

Article published online:
09 May 2023

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