A new approach to phorbol by [4 + 3] oxyallyl cycloaddition and intramolecular Heck reaction.
[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.
Lee
K
K
Department of Chemistry, University of Alabama, Tuscaloosa 35487, USA.
Cha
J K
JK
D000498:Allyl Compounds / Q000737:chemistry*; D003500:Cyclization; D010704:Phorbols / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000498:Allyl Compounds; D010704:Phorbols