2002 other bioactive products

other bioactive productsU 1300

04 - 246Enantioselective Synthesis of Imperanene, a Platelet AggregationInhibitor. — Both enantiomers of imperanene (VIII) are accessibleusing Enders’ SAMP/RAMP chiral auxiliary method for the diastereoselectivealkylation of aldehyde (II). After removal of the chiral auxiliary, the opticalpurity of the alkylation product (VII) and its enantiomer is determined tobe 82-90% e.e. Comparison of the data of enantiomers (R)- and (S)-(VIII)with those of previously isolated imperanene reveals the (S)-enantiomer tobe the naturally occurring isomer. — (SHATTUCK, JAMES C.; SHREVE,CHENEY M.; SOLOMON, SANDRA E.; Org. Lett. 3 (2001) 19, 3021-3023;Dep. Chem., Univ. Hartford, West Hartford, CT 06117, USA; EN)

1