Sequential cycloaddition approach to the tricyclic core of vibsanin E. Total synthesis of (+/-)-5-epi-10-epi-vibsanin E.
[chemical reaction: see text]. A direct access to (+/-)-5-epi-10-epi-vibsanin E is described, based on three key cycloaddition steps, a rhodium-catalyzed [4 + 3] cycloaddition, a heteronuclear [4 + 2] cycloaddition, and a photochemically induced [4 + 2] cycloaddition.
Davies
Huw M L
HM
Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260-3000, USA. hdavies@buffalo.edu
Loe
Øystein
Ø
Stafford
Douglas G
DG
D002384:Catalysis; D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010777:Photochemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
C512546:5-epi-10-epi-vibsanin E; D004224:Diterpenes; D012238:Rhodium