Total Synthesis of the Immunosupressant (−)-Pironetin (PA48153C)

Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned. Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selectiv...

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Bibliographic Details
Published in:Organic letters 2001-03, Vol.3 (5), p.707-710
Main Authors: Keck, Gary E, Knutson, Chad E, Wiles, Sarah A
Format: Article
Language:English
Subjects:
Immunosuppressive Agents - chemical synthesis
Indicators and Reagents
Pyrones - chemical synthesis
Streptomyces - chemistry
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Summary:Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned. Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective SmI2 reduction of a β-hydroxyketone, and finally a lactone annulation reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015531m