First enantioselective total synthesis and configurational assignments of suberosenone and suberosanone as potential antitumor agents

Mohammad Kousara; Angélique Ferry; Franck Le Bideau; Kathalyn L Serré; Isabelle Chataigner; Estelle Morvan; Joëlle Dubois; Monique Chéron; Françoise Dumas

doi:10.1039/c4cc10041g

First enantioselective total synthesis and configurational assignments of suberosenone and suberosanone as potential antitumor agents

Chem Commun (Camb). 2015 Feb 25;51(16):3458-61. doi: 10.1039/c4cc10041g.

Authors

Mohammad Kousara¹, Angélique Ferry, Franck Le Bideau, Kathalyn L Serré, Isabelle Chataigner, Estelle Morvan, Joëlle Dubois, Monique Chéron, Françoise Dumas

Affiliation

¹ CNRS-BioCIS UMR 8076, Chimie des Substances Naturelles, IPSIT and LabEx LERMIT, Faculté de Pharmacie, Université de Paris Sud, 5, rue J.-B. Clément, 92296 Châtenay-Malabry, France. [email protected].

PMID: 25626720
DOI: 10.1039/c4cc10041g

Abstract

The first enantioselective total syntheses of two marine sesquiterpenes (1R)-suberosenone and (1R)-suberosanone are achieved leading to revision of the AC of natural (1S)-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Chemistry Techniques, Synthetic
Humans
Sesquiterpenes / chemical synthesis*
Sesquiterpenes / chemistry
Sesquiterpenes / pharmacology*
Stereoisomerism

Substances

Antineoplastic Agents
Sesquiterpenes
suberosanone
suberosenone