First total synthesis and structural reassignment of (-)-aplysiallene.
The first total synthesis of (-)-aplysiallene has been completed in 16 steps and features a key sequential Mukaiyama aerobic oxidative cyclization to prepare the fused bis-THF core. The original stereochemical assignment has been revised as shown.
Wang
Jian
J
Department of Chemistry, University of Western Ontario, 1151 Richmond Street, London, ON, N6A 5B7, Canada.
Pagenkopf
Brian L
BL
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D005663:Furans; C432927:aplysiallene