Stereoselective synthesis of 3-aminoindan-1-ones and subsequent incorporation into HIV-1 protease inhibitors.
A new method for the stereoselective synthesis of 3-aminoindan-1-ones from triflates of salicylic sulfinyl imines and ethylene glycol vinyl ether has been developed. The reaction sequence starts with a regioselective Heck reaction followed by stereoselective Lewis acid mediated annulation. Acidic cleavage of the sulfinamides produced pure (R)- and (S)-3-aminoindan-1-ones, which were successfully isolated and incorporated into active HIV-1 protease inhibitors.
Arefalk
Anna
A
Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala University, BMC, P.O. Box-574, SE-751 23 Uppsala, Sweden.
Wannberg
Johan
J
Larhed
Mats
M
Hallberg
Anders
A
D017320:HIV Protease Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D007097:Imines / Q000737:chemistry; D007189:Indans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
D017320:HIV Protease Inhibitors; D007097:Imines; D007189:Indans; D013450:Sulfones