TY - JOUR AU - Kousara, Mohammad; Bideau, Franck Le; Ibrahim, Rama; Ferry, Angélique; Venot, Pierre-Etienne; Dejean, Camille; Raingeaud, Joël; Dubois, Joëlle; Retailleau, Pascal; Dumas, Françoise TI - Suberosanes as Potential Antitumor Agents: First Enantioselective Total Synthesis of (1S)-Suberosanone and Configurational Assignment of Suberosenol A SN - 0039-7881 SN - 1437-210X PY - 2016 JO - Synthesis JF - Synthesis LA - EN VL - 48 IS - 11 SP - 1637 EP - 1646 ET - 2016/04/20 DA - 2016/05/17 KW - antitumor agents KW - chemoselectivity KW - marine natural products KW - configuration determination KW - asymmetric synthesis KW - total synthesis AB - 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. PB - © Georg Thieme Verlag DO - 10.1055/s-0035-1561430 UR - http://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-0035-1561430 ER -