title: An asymmetric synthesis of aza analogues of the tricyclic skeleton of daphnane and the ABC ring system of phorbol.
abstract: An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.
authors.affiliation: Rhône-Poulenc Rorer Ltd., Rainham Road South, Dagenham, Essex RM10 7XS, UK.
authors.forename: Charles M
authors.initials: CM
authors.lastname: Marson
authors.forename: Jennifer H
authors.initials: JH
authors.lastname: Pink
authors.forename: David
authors.initials: D
authors.lastname: Hall
authors.forename: Michael B
authors.initials: MB
authors.lastname: Hursthouse
authors.forename: Abdul
authors.initials: A
authors.lastname: Malik
authors.forename: Christopher
authors.initials: C
authors.lastname: Smith
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D018360:Crystallography, X-Ray; D003500:Cyclization; D004224:Diterpenes; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010704:Phorbols / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
chemical_list: D001372:Aza Compounds; D004224:Diterpenes; D010704:Phorbols; D013729:Terpenes; C011309:mezerein; C033085:phorbol