title: Expedient enantioselective synthesis of cermizine D.
abstract: An efficient enantioselective synthesis of cermizine D has been developed that exploits the use of a common intermediate to access over 85% of the carbon backbone. Key steps include an organocatalyzed heteroatom Michael addition, a diastereoselective alkylation with α-iodomethyl phenyl sulfide, a conjugate addition to a vinyl sulfone species, and a sulfone coupling/desulfurization sequence to join the two major subunits.
authors.affiliation: Department of Chemistry, 153 Gilbert Hall, Oregon State University, Corvallis, Oregon 97331, United States.
authors.forename: Nagarathanam
authors.initials: N
authors.lastname: Veerasamy
authors.forename: Erik C
authors.initials: EC
authors.lastname: Carlson
authors.forename: Rich G
authors.initials: RG
authors.lastname: Carter
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000478:Alkylation; D002384:Catalysis; D003500:Cyclization; D032502:Lycopodium / Q000737:chemistry; D015394:Molecular Structure; D054837:Quinolizidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D000470:Alkaloids; D054837:Quinolizidines; D013450:Sulfones; C529947:cermizine D; C009873:divinyl sulfone