Stereoselective synthesis of (+/-)-rocaglaol analogues.
An intramolecular hydroxy epoxide opening was used to access the cyclopenta[b]benzofuran ring system of the natural product rocaglaol (2). Our route allowed the stereocontrolled preparation of the rocaglaol derivative (+/-)-(1S*,3S*,3aR*,8bS*)-3b. The synthesis of the (+/-)-(3R*)-epimer of 3b was also achieved. Our strategy is well-suited for the production of analogues with variation of the western ring. [reaction: see text]
Thede
Kai
K
Medicinal Chemistry, Pharma Research, Bayer HealthCare AG, 42096 Wuppertal, Germany.
Diedrichs
Nicole
N
Ragot
Jacques P
JP