Expedient synthesis of (+/-)-bipinnatin J.
[reaction: see text] A nine-step, stereoselective synthesis of bipinnatin J is described, which features a ruthenium-catalyzed Alder-ene reaction, a Stille cross coupling, and an intramolecular Nozaki-Hiyama-Kishi allylation as key steps. The biosynthetic relationship between bipinnatin J and complex polycyclic diterpenes isolated from gorgonian corals is discussed.
Roethle
Paul A
PA
Department of Chemistry, University of California, Berkeley, 94720, USA.
Trauner
Dirk
D
D000818:Animals; D037421:Anthozoa / Q000737:chemistry; D002384:Catalysis; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D004224:Diterpenes; C513883:bipinnatin J