title: A strategy toward the synthesis of C13-oxidized cembrenolides.
abstract: An efficient strategy for the construction of C13-oxidized cembrenolides is reported. Central to this strategy is the installation of the C13hydroxyl group prior to cembrane macrocyclization (via formation of the C1-C2bond), allowing access to both C13alcohol epimers. The orientation of the C13alcohol was found to influence the cyclization mode of the cembranolide scaffold upon furan oxidation, leading to motifs reminiscent to bipinnatolide F, bielschowskysin, and verrillin.
authors.affiliation: Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093-0358, United States.
authors.forename: Alec
authors.initials: A
authors.lastname: Saitman
authors.forename: Steven D E
authors.initials: SD
authors.lastname: Sullivan
authors.forename: Emmanuel A
authors.initials: EA
authors.lastname: Theodorakis
keywords: Anomeric effect; Cembrane; Furan oxidation; Hemiketal; Macrocyclization