Enantioselective synthesis of imperanene, a platelet aggregation inhibitor.
Both enantiomers of imperanene, a platelet aggregation inhibitor, have been synthesized in 82-90% ee. The key step of establishing the chiral center was achieved through stereoselective alkylation with benzyl chloromethyl ether using Enders' RAMP/SAMP chiral auxiliary method. The natural product was determined to be the (S)-enantiomer through comparison of optical rotation data. Reaction: see text.
Shattuck
J C
JC
Department of Chemistry, University of Hartford, West Hartford, Connecticut 06117-1599, USA. shattuck@mail.hartford.edu
Shreve
C M
CM
Solomon
S E
SE
D000478:Alkylation; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry; D004232:Diuretics / Q000138:chemical synthesis / Q000737:chemistry; D009904:Optical Rotation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*; D010946:Plants, Medicinal / Q000737:chemistry; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D000893:Anti-Inflammatory Agents; D004232:Diuretics; D010636:Phenols; D010975:Platelet Aggregation Inhibitors; C093767:imperanene