Mohammad Kousara, Franck Le Bideau, Rama Ibrahim, Angélique Ferry, Pierre-Etienne Venot, Camille Dejean, Joël Raingeaud, Joëlle Dubois, Pascal Retailleau, Françoise Dumas*
The first enantioselective total syntheses of two marine sesquiterpenes natural (1S)-suberosanone and (1S)-suberosenol A are achieved leading to assignment of the absolute configuration of natural suberosenol A. Also described, a new access to (1S)-suberosenone from a key tricyclic enone was developed leading to an overall improvement of the synthesis allowing an efficient access to suberosenol A. Hyperbaric asymmetric Michael addition and a highly efficient silver trifluoroacetate mediated alpha-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 remaining to be elucidated.
https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0035-1561430