Formal synthesis of (+/-)-guanacastepene A: a tandem ring-closing metathesis approach.
A concise route to a key intermediate in the total synthesis of guanacastepene A is described. The main features include the simultaneous construction of the seven- and six-membered rings, using a tandem ring-closing metathesis and a stereoselective introduction of the oxygenated function at the C5 position. [reaction: see text]
Boyer
François-Didier
FD
Unité de Phytopharmacie et Médiateurs Chimiques, I.N.R.A., Route de Saint-Cyr, F-78026 Versailles, France.
Hanna
Issam
I
Ricard
Louis
L
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D005658:Fungi / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D004224:Diterpenes; C454620:guanacastepene A