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DOI: 10.1055/a-1546-2572
Bioinspired Total Synthesis of Marine Anticancer Meroterpenoids Dysideanone B and Dysiherbol A and Structure Revision of Dysiherbol A
We acknowledge the National Natural Science Foundation of China (21971121), the Open Project of State Key Laboratory of Natural Medicines (SKLNMKF201909) and the Fundamental Research Funds for the Central Universities, Nankai University (63191140, 63201109) for financially support. We thank the State Key Laboratory of Medicinal Chemical Biology (SKLMCB) and College of Pharmacy at Nankai University (NKU) for supporting our research.
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 synthesisPublication 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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