title: Total synthesis of norcembrenolide B and scabrolide D.
abstract: An efficient stereoselective synthesis of norcembrenolide B (8) and scabrolide D (9) is reported. The strategy is inspired by biogenetic relationships of related cembrenoids. Central to this approach is the construction of norbipinnatin J which upon selective C2 deoxygenation and C8 oxygenation produces norrubifolide and norcoralloidolide A. A sequence of site-selective oxidations and skeletal reorganizations then yields, in a divergent manner, compounds 8 and 9. The studies allow revision of the proposed structure of scabrolide D (9), which is identical to norcembrenolide C.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive MC: 0358, La Jolla, California 92093-0358, USA.
authors.forename: Alec
authors.initials: A
authors.lastname: Saitman
authors.forename: Pauline
authors.initials: P
authors.lastname: Rulliere
authors.forename: Steven D E
authors.initials: SD
authors.lastname: Sullivan
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis
mesh_terms: D004224:Diterpenes / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D004224:Diterpenes; C477929:norcembrenolide; C569336:norcembrenolide B; C569335:scabrolide D