Synthesis of (+)-4-desoxypentenomycin and analogues

Synthesis of (+)-4-desoxypentenomycin and analogues

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 a...

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Main Authors: Supakeat Kambutong, Chutima Kuhakarn, Patoomratana Tuchinda, Manat Pohmakotr
Other Authors: Mahidol University
Format: Article
Published: 2018
Subjects:
Chemical Engineering
Chemistry
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/28892
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spelling th-mahidol.288922018-09-24T15:53:43Z Synthesis of (+)-4-desoxypentenomycin and analogues Supakeat Kambutong Chutima Kuhakarn Patoomratana Tuchinda Manat Pohmakotr Mahidol University Chemical Engineering Chemistry 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. 2018-09-24T08:51:25Z 2018-09-24T08:51:25Z 2010-08-13 Article Synthesis. No.9 (2010), 1453-1458 10.1055/s-0029-1218690 1437210X 00397881 2-s2.0-77955364958 https://repository.li.mahidol.ac.th/handle/123456789/28892 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=77955364958&origin=inward
institution Mahidol University
building Mahidol University Library
continent Asia
country Thailand
Thailand
content_provider Mahidol University Library
collection Mahidol University Institutional Repository
topic Chemical Engineering
Chemistry
spellingShingle Chemical Engineering
Chemistry
Supakeat Kambutong
Chutima Kuhakarn
Patoomratana Tuchinda
Manat Pohmakotr
Synthesis of (+)-4-desoxypentenomycin and analogues
description 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.
author2 Mahidol University
author_facet Mahidol University
Supakeat Kambutong
Chutima Kuhakarn
Patoomratana Tuchinda
Manat Pohmakotr
format Article
author Supakeat Kambutong
Chutima Kuhakarn
Patoomratana Tuchinda
Manat Pohmakotr
author_sort Supakeat Kambutong
title Synthesis of (+)-4-desoxypentenomycin and analogues
title_short Synthesis of (+)-4-desoxypentenomycin and analogues
title_full Synthesis of (+)-4-desoxypentenomycin and analogues
title_fullStr Synthesis of (+)-4-desoxypentenomycin and analogues
title_full_unstemmed Synthesis of (+)-4-desoxypentenomycin and analogues
title_sort synthesis of (+)-4-desoxypentenomycin and analogues
publishDate 2018
url https://repository.li.mahidol.ac.th/handle/123456789/28892
_version_ 1763497315976347648

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