First enantioselective total synthesis and configurational assignments of suberosenone and suberosanone as potential antitumor agents. Issue 16 (28th January 2015)

• Record Type: Journal Article
• Authors: Kousara, Mohammad; Ferry, Angélique; Le Bideau, Franck; Serré, Kathalyn L.; Chataigner, Isabelle; Morvan, Estelle; Dubois, Joëlle; Chéron, Monique; Dumas, Françoise
• Is Part Of: Chemical communications. Volume 51:Issue 16(2015)
• Page Start: 3458
• Page End: 3461
• Publication Date: 2015-01-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c4cc10041g
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : The first enantioselective syntheses of (1 R )-suberosenone and (1 R )-suberosanone are achieved, leading to revision of the AC of a natural (1 S )-suberosanone. Abstract : The first enantioselective total syntheses of two marine sesquiterpenes (1 R )-suberosenone and (1 R )-suberosanone are achieved leading to revision of the AC of natural (1 S )-suberosanone. Key elements of the synthesis include hyperbaric asymmetric Michael addition and highly efficient silver trifluoroacetate mediated α-alkylation for the formation of ring A.