Total synthesis of the immunosupressant (-)-pironetin (PA48153C)

Authors
Keck, GE Knutson, CE Wiles, SA
Citation
Ge. Keck et al., Total synthesis of the immunosupressant (-)-pironetin (PA48153C), ORG LETT, 3(5), 2001, pp. 707-710
Citations number
26
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
5
Year of publication
2001
Pages
707 - 710
Database
ISI
SICI code
1523-7060(20010308)3:5<707:TSOTI(>2.0.ZU;2-H
Abstract
[GRAPHICS] Total synthesis of the immunosuppresant pironetin has been achieved by a sy nthetic route in which the connections between starting materials and the d esired structure are readily discerned, Key steps include a diastereoselect ive Lewis acid mediated crotylstannane aldehyde addition, a highly selectiv e Lewis acid promoted Mukaiyama aldol reaction, an anti-selective Sml(2) re duction of a beta -hydroxyketone, and finally a lactone annulation reaction .