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Synthesis 2010(9): 1453-1458  
DOI: 10.1055/s-0029-1218690
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-4-Desoxypentenomycin and Analogues

Supakeat Kambutong, Chutima Kuhakarn, Patoomratana Tuchinda, Manat Pohmakotr*
Department of Chemistry and Center for Innovation in Chemistry (PERCH-CIC), Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400, Thailand
Fax: +66(2)6445126; e-Mail: scmpk@mahidol.ac.th;
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Publication History

Received 26 January 2010
Publication Date:
09 March 2010 (online)

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Abstract

A synthesis of (+)-4-desoxypentenomycin is reported here; it involves diastereoselective phenylsulfanylpropylation of an enolate anion derived from methyl (2R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carboxylate, obtained from d-mannitol, and is followed by sulfide oxidation, intramolecular acylation of the α-sulfinyl carbanion, sulfoxide elimination, and hydrolysis. Straightforward access to substituted analogues of (+)-4-desoxypentenomycin was also demonstrated by means of Suzuki-Miyaura, Sonogashira, and Heck coupling reactions.

Key words

oxygenated cyclopentenones - desoxycyclopentenones - α-sulfinyl carbanions - cyclizations - asymmetric synthesis

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