Enantioselective synthesis of imperanene, a platelet aggregation inhibitor

Authors
Shattuck, JC Shreve, CM Solomon, SE
Citation
Jc. Shattuck et al., Enantioselective synthesis of imperanene, a platelet aggregation inhibitor, ORG LETT, 3(19), 2001, pp. 3021-3023
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
19
Year of publication
2001
Pages
3021 - 3023
Database
ISI
SICI code
1523-7060(20010920)3:19<3021:ESOIAP>2.0.ZU;2-1
Abstract
[GRAPHICS] Both enantiomers of imperanene, a platelet aggregation inhibitor, have been synthesized in 82-90% ee. The key step of establishing the chiral center w as achieved through stereoselective alkylation with benzyl chloromethyl eth er using Enders' RAMP/SAMP chiral auxiliary method. The natural product was determined to be the (S)-enantiomer through comparison of optical rotation data.