title: Total synthesis of kopsinine.
abstract: The use of a powerful intramolecular [4 + 2]/[3 + 2] cycloaddition cascade of an 1,3,4-oxadiazole in the divergent total synthesis of kopsinine (1), featuring an additional unique SmI(2)-promoted transannular cyclization reaction for formation of the bicyclo[2.2.2]octane central to its hexacyclic ring system, is detailed.
authors: Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
authors: Jian
authors: J
authors: Xie
authors: Amanda L
authors: AL
authors: Wolfe
authors: Dale L
authors: DL
authors: Boger
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009795:Octanes / Q000737:chemistry; D010069:Oxadiazoles / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D026121:Indole Alkaloids; D009795:Octanes; D010069:Oxadiazoles; C061491:kopsinine; C026728:octane
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