title: Formal synthesis of merrilactone A using a domino cyanide 1,4-addition-aldol cyclization.
abstract: A formal synthesis of merrilactone A has been completed using a domino 1,4-addition-aldol process as the key step. Both iodo- and cyano-1,4-addition-aldol cyclizations were productive in forming the highly hindered C1-C9 bond linking vic-quaternary and tertiary stereocenters. The latter method was used to complete a formal total synthesis of the natural product.
authors: School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K., School of Chemistry, University of Edinburgh , Joseph Black Building, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, U.K., and AstraZeneca , Mereside, Alderley Park, Macclesfield, Cheshire SK10 4TG, U.K.
authors: Naim
authors: N
authors: Nazef
authors: Robert D M
authors: RD
authors: Davies
authors: Michael F
authors: MF
authors: Greaney
mesh_terms: D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003486:Cyanides; D007783:Lactones; D012717:Sesquiterpenes; C458341:merrilactone A