Biological Evaluations, NMR Analyses, Molecular Modeling Studies, and Overview of the Synthesis of the Marine Natural Product (−)-Mucosin
Jens M. J. Nolsøe,
Jarl Underhaug,
Åshild Moi Sørskar,
Simen Gjelseth Antonsen,
Karl E. Malterud,
Osman Gani,
Qiong Fan,
Marit Hjorth,
Thomas Sæther,
Trond V. Hansen,
Yngve H. Stenstrøm
Affiliations
Jens M. J. Nolsøe
Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway
Jarl Underhaug
Department of Chemistry, University of Bergen, Allégaten 41, NO-5007 Bergen, Norway
Åshild Moi Sørskar
Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway
Simen Gjelseth Antonsen
Department of Mechanical, Electronic and Chemical Engineering, Faculty of Technology, Art and Design, Oslo Metropolitan University, NO-0130 Oslo, Norway
Karl E. Malterud
Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway
Osman Gani
Department of Pharmacy, Section for Pharmaceutical Chemistry, University of Oslo, P.O. Box 1068, NO-0316 Oslo, Norway
Qiong Fan
Department of Molecular Medicine, Institute of Basic Medical Sciences, Faculty of Medicine, University of Oslo, NO-0317 Oslo, Norway
Marit Hjorth
Department of Molecular Medicine, Institute of Basic Medical Sciences, Faculty of Medicine, University of Oslo, NO-0317 Oslo, Norway
Thomas Sæther
Department of Molecular Medicine, Institute of Basic Medical Sciences, Faculty of Medicine, University of Oslo, NO-0317 Oslo, Norway
Trond V. Hansen
Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway
Yngve H. Stenstrøm
Faculty of Chemistry, Biotechnology and Food Science, Norwegian University of Life Sciences, P.O. Box 5003, NO-1433 Ås, Norway
Natural products obtained from marine organisms continue to be a rich source of novel structural architecture and of importance in drug discovery, medicine, and health. However, the success of such endeavors depends on the exact structural elucidation and access to sufficient material, often by stereoselective total synthesis, of the isolated natural product of interest. (−)-Mucosin (1), a fatty acid derivative, previously presumed to contain a rare cis-bicyclo[4.3.0]non-3-ene moiety, has since been shown to be the trans-congener. Analytically, the fused bicyclic ring system in (−)-1 constitutes a particular challenge in order to establish its relative and absolute stereochemistry. Herein, data from biological evaluations, NMR and molecular modeling studies of (−)-1 are presented. An overview of the synthetic strategies enabling the exact structural elucidation of (−)-mucosin (1) is also presented.
