Publication: Synthesis of (+)-4-desoxypentenomycin and analogues
Issued Date
2010-08-13
Resource Type
ISSN
1437210X
00397881
00397881
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2-s2.0-77955364958
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Mahidol University
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SCOPUS
Bibliographic Citation
Synthesis. No.9 (2010), 1453-1458
Suggested Citation
Supakeat Kambutong, Chutima Kuhakarn, Patoomratana Tuchinda, Manat Pohmakotr Synthesis of (+)-4-desoxypentenomycin and analogues. Synthesis. No.9 (2010), 1453-1458. doi:10.1055/s-0029-1218690 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/28892
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Title
Synthesis of (+)-4-desoxypentenomycin and analogues
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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 a-sulfinyl carbanion, sulfoxide elimination, and hydrolysis. Straightforward access to substituted analogues of (+)-4-desoxy-pentenomycin was also demonstrated by means of Suzuki-Miyaura, Sonogashira, and Heck coupling reactions. © Georg Thieme Verlag Stuttgart.