Highly Diastereoselective Route to α‑Glucosidase Inhibitors, Neosalacinol and Neoponkoranol

A facile and highly diastereoselective route to potent natural α-glucosidase inhibitors, i.e., neosalacinol (4) and neoponkoranol (6), isolated from the traditional Ayurvedic medicine “Salacia” was developed by intramolecular cyclization of appropriately substituted sulfides (9 and 12).

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Bibliographic Details
Published inJournal of organic chemistry Vol. 81; no. 8; pp. 3407 - 3415
Main Authors Tanabe, Genzoh, Matsuda, Youya, Oka, Misato, Kunikata, Yousuke, Tsutsui, Nozomi, Xie, Weija, Balakishan, Gorre, Amer, Mumen F. A, Marumoto, Shinsuke, Muraoka, Osamu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.04.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cyclization
Glycoside Hydrolase Inhibitors - chemistry
Glycoside Hydrolase Inhibitors - pharmacology
Physical Sciences
Plant Extracts - chemistry
Plant Extracts - isolation & purification
Salacia - chemistry
Science & Technology
Stereoisomerism
Structure-Activity Relationship
Sugar Alcohols - chemistry
Sugar Alcohols - pharmacology
Sulfates - chemistry
Sulfates - pharmacology
Sulfides - chemistry
Thiophenes - chemistry
Thiophenes - pharmacology
REVISION
ANALOGS
SIDE-CHAIN
GLYCOSIDASE INHIBITOR
SULFONIUM SULFATE STRUCTURE
MEDICINE SALACIA-RETICULATA
BIOLOGICAL EVALUATION
KOTALANOL
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Summary:A facile and highly diastereoselective route to potent natural α-glucosidase inhibitors, i.e., neosalacinol (4) and neoponkoranol (6), isolated from the traditional Ayurvedic medicine “Salacia” was developed by intramolecular cyclization of appropriately substituted sulfides (9 and 12).
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b02894