Exploring biosynthetic relationships among furanocembranoids: synthesis of (-)-bipinnatin J, (+)-intricarene, (+)-rubifolide, and (+)-isoepilophodione B.
The asymmetric total synthesis of (-)-bipinnatin J and its conversion into (+)-intricarene through a transannular 1,3-dipolar cycloaddition is described. In addition, the conversion of (-)-bipinnatin J into (+)-rubifolide and (+)-isoepilophodione B is reported. Biosynthetic relationships among furanocembranoids and the possible role of 1,3-dipolar cycloadditions in biosynthesis are discussed. [reaction: see text]
Roethle
Paul A
PA
Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Hernandez
Paul T
PT
Trauner
Dirk
D
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014315:Triterpenes / Q000138:chemical synthesis*
D004224:Diterpenes; D014315:Triterpenes; C513883:bipinnatin J; C507581:intricarene; C522319:isoepilophodione B; C522318:rubifolide