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Synthesis 2011(3): 451-458  
DOI: 10.1055/s-0030-1258389
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© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Stagonolide G from d-Mannitol

Chebolu Naga Sesha Sai Pavan Kumar, Mettu Ravinder, Singam Naveen Kumar, Vaidya Jayathirtha Rao*
Organic Chemistry Division-II, Indian Institute of Chemical Technology, Uppal Road, Tarnaka, Hyderabad 500607, India
Fax: +91(40)27160757; e-Mail: jrao@iict.res.in;
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Publication History

Received 15 October 2010
Publication Date:
05 January 2011 (online)

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Stereoselective Synthesis of Stagonolide G from d-MannitolSynthesis 2011; 2011(08): 1320-1320
DOI: 10.1055/s-0030-1259985

Abstract

A highly convergent, stereoselective total synthesis of a ten-membered lactone, stagonolide G, is described. Epoxide ring-opening with vinyl Grignard, Yamaguchi esterification and ring-closing metathesis are the key steps involved in the present approach. d-Mannitol was used as a chiral pool material for the construction of both of the key fragments - the olefinic acid and the olefinic alcohol moieties.

Key words

chiral pool - Grignard reaction - esterification - ring closure - macrocycles

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