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Synlett 2009(17): 2828-2830  
DOI: 10.1055/s-0029-1217974
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of (+)-Aspicilin from d-Mannitol

J. S. Yadav*, T. Srinivasa Rao, K. Ravindar, B. V. Subba Reddy
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27160512; e-Mail: yadavpub@iict.res.in;
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Publication History

Received 16 June 2009
Publication Date:
09 September 2009 (online)

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Abstract

The total synthesis of the 18-membered lichen macrolide, (+)-aspicilin, has been accomplished utilizing the Swern oxidation, Masamune-Roush olefination, and ring-closing metathesis of a trienic ester as key steps. d-Mannitol has been utilized as the chiral pool material for the construction of the olefinic aldehyde and the Jacobsen hydrolytic kinetic resolution has been employed for the construction of the olefinic phosphonate ester.

Key words

(+)-aspicilin - Swern - Masamune-Roush olefination - ring-closing metathesis - d-mannitol - kinetic resolution

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Experimental procedures and spectral data for selected compounds are given in the Supporting Information.