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Synthesis 2012(4): 585-590  
DOI: 10.1055/s-0031-1290156
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of Putaminoxin

Jhillu Singh Yadav*a,b, Ande Rajua,c, Kontham Ravindara, Basi V. Subba Reddya, Ahmad Al Khazim Al Ghamdib
a Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
b Engineer Abdullah Baqshan for Bee Research, King Saudi University, Saudi Arabia
c University of Hyderabad, Hyderabad 500046, India
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Publikationsverlauf

Received 14 October 2011
Publikationsdatum:
16. Januar 2012 (online)

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Abstract

The stereoselective total synthesis of a phytotoxic macrolide putaminoxin, isolated from the culture of Phoma putaminum fungus, has been accomplished by utilization of Sharpless asymmetric epoxidation, Birch reduction, Jacobsen’s kinetic resolution of racemic epoxide, and Yamaguchi lactonization as key transformations.

Key words

macrolide - necrotic leaf disease - Sharpless asymmetric epoxidation - Birch reduction - Jacobsen’s kinetic resolution - Yamaguchi lactonization

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