Synthesis 2008(24): 3945-3950  
DOI: 10.1055/s-0028-1083249
PAPER
© 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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Publikationsverlauf

Received 9 July 2008
Publikationsdatum:
01. Dezember 2008 (online)

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.