title: A new approach to phorbol by [4 + 3] oxyallyl cycloaddition and intramolecular Heck reaction.
abstract: [formula: see text] A new synthetic strategy for a functionalized tricyclic core of phorbol has been developed by means of a [4 + 3] oxyallyl cycloaddition and subsequent intramolecular Heck reaction. The [4 + 3] oxyallyl cycloadduct 7 was chosen as the B-ring precursor of phorbol. Subsequent elaboration took advantage of its well-defined diastereofacial bias to afford the tricycle 5. This method should be of general value in the construction of 6,7- or 5,7-fused bicyclic systems.
authors.affiliation: Department of Chemistry, University of Alabama, Tuscaloosa 35487, USA.
authors.forename: K
authors.initials: K
authors.lastname: Lee
authors.forename: J K
authors.initials: JK
authors.lastname: Cha
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D003500:Cyclization; D010704:Phorbols / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000498:Allyl Compounds; D010704:Phorbols