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Synthesis 2011(5): 755-758  
DOI: 10.1055/s-0030-1258418
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Formal Total Synthesis of (-)-Swainsonine from Garner’s Aldehyde

Sabbavarapu Narayana Murthy, Yadavalli Venkata Durga Nageswar*
Organic Chemistry Divison-I, Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: dryvdnageswar@gmail.com;
Further Information

Publication History

Received 2 December 2010
Publication Date:
21 January 2011 (online)

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Abstract

A simple and facile stereoselective formal total synthesis of (-)-swainsonine has been reported starting from Garner’s l-serine derived oxazolidine aldehyde. Our synthetic strategy involves stereoselective allylation and Still olefination as key intermediary reaction steps.

Key words

swainsonine - indium - allylation - Garner’s aldehyde - Still olefination - indolizidine alkaloid

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