Synthesis of the [5-7-6] tricyclic core of guanacastepene A via an intramolecular Mukaiyama aldol reaction.
[reaction: see text] A synthesis of the tricyclic [5-7-6] skeleton of guanacastepene A is described. The six-membered ring of guanacastepene A was constructed by a Diels-Alder reaction. After several functional group transformations, it was coupled to beta-iodocyclopentenone. Lithium dimethylcuprate conjugate addition followed by an intramolecular Mukaiyama aldol reaction furnished the desired [5-7-6] tricyclic ring system.
Du
Xiaohui
X
Department of Chemistry & Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, USA.
Chu
Hiufung V
HV
Kwon
Ohyun
O
D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation
D004224:Diterpenes; D007202:Indicators and Reagents; C409194:guanacastepene