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Synthesis 2008(24): 3945-3950  
DOI: 10.1055/s-0028-1083249
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© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Formal Synthesis of Herbarumin III via Prins Cyclization

J. S. Yadav*, Hissana Ather, K. Uma Gayathri, N. Venkateswar Rao, A. R. Prasad
Pheromone Group, Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 9 July 2008
Publication Date:
01 December 2008 (online)

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Abstract

The total synthesis of herbarumin III is described, proving the versatility of the Prins cyclization in the synthesis of natural products. The approach is convergent and highly stereoselective. Ring-closing metathesis and alkene-rearrangement reactions are utilized as key steps in the synthesis of the macrolactone.

Key words

herbarumins - Prins cyclization - alkene rearrangement - ring-closing metathesis

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