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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Errata Practical and Scalable Total Syntheses of (+)-Dysidavarones A–CSynlett 2024; 35(05): e2-e2
DOI: 10.1055/s-0043-1763686

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.

Key words

total synthesis - natural products - dysidavarones - sesquiterpene quinones - meroterpenoids

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2066-0860.
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Publication History

Received: 28 February 2023

Accepted after revision: 30 March 2023

Accepted Manuscript online:
30 March 2023

Article published online:
09 May 2023

© 2023. Thieme. All rights reserved

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