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Synlett 2010(20): 3078-3080  
DOI: 10.1055/s-0030-1259056
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Total Synthesis of Achaetolide from d-Mannitol

K. Sripad Rao, Amit Kumar Chattapadhyay, Subhash Ghosh*
Organic Chemistry Division III, Indian Institute of Chemical Technology, Hyderabad 500607, India
Fax: +91(40)27193108; e-Mail: subhash@iict.res.in;
Further Information

Publication History

Received 4 October 2010
Publication Date:
19 November 2010 (online)

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Abstract

A highly convergent stereoselective total synthesis of achaetolide, a ten-membered lactone is described. The ring-closing metathesis reaction was used to construct the macrocycle and E-olefinic moiety in the molecule. The key acid and alcohol fragments were synthesized from a single chiral pool material d-mannitol.

Key words

Achaetominum cristalliferum - Ophiobolus sp. - achaetolide - d-mannitol - ring-closing metathesis

    References and Notes

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