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Abstract

The first enantioselective total syntheses of two marine sesquiterpenes, natural (1S)-suberosanone and (1S)-suberosenol A, are achieved leading to the assignment of the absolute configuration of natural suberosenol A. A new access to (1S)-suberosenone from a key tricyclic enone was also developed leading to an overall improvement of the synthesis, allowing an efficient route to suberosenol A. Hyperbaric asymmetric Michael addition and a highly efficient silver trifluoroacetate mediated α-alkylation for the formation of ring A completed the key steps of the synthesis. Regrettably, synthetic (1S)-suberosanone did not retain the reported picomolar cytotoxic activity displayed by the natural product, the reason for which remains to be elucidated.

Journal Article

https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0035-1561430