Six-Step Syntheses of (−)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N‑Z‑O‑TBDPS‑l‑serinal

Highly stereoselective six-step syntheses of (−)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by...

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Published inJournal of organic chemistry Vol. 81; no. 21; pp. 10569 - 10575
Main Authors Kawamura, Meire Y, Talero, Alexánder G, Santiago, João V, Garambel-Vilca, Edson, Rosset, Isac G, Burtoloso, Antonio C. B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1-DEOXYALTRONOJIRIMYCIN
ACID-DERIVATIVES
ASYMMETRIC-SYNTHESIS
1-DEOXYNOJIRIMYCIN
NATURAL OCCURRENCE
STEREOSELECTIVE-SYNTHESIS
INDOLIZIDINES
PIPERIDINES
H INSERTION REACTIONS
ALPHA,BETA-UNSATURATED DIAZOKETONES
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Summary:Highly stereoselective six-step syntheses of (−)-1-deoxyaltronojirimycin (altro-DNJ) and (+)-1-deoxymannojirimycin (manno-DNJ) from N-Cbz-O-TBDPS-l-serinal are described. Key transformations involve a two-step preparation of a functionalized dihydropyridin-3-one as a common intermediate followed by Luche reduction and dihydroxylation (for altro-DNJ). The same sequence employing an epoxidation/epoxide opening in place of dihydroxylation furnishes manno-DNJ.
Bibliography:FAPESP
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b01575