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Asymmetric synthesis of (+)-1-deoxynojirimycin

✍ Scribed by Ulf M. Lindström; Peter Somfai

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
205 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

An asymmetric synthesis of (+)-l-deoxynojirimycin (1) in 14 steps starting from diene ( 5) is described. The key transformations in the sequence are a Sharpless dihydroxylation and epoxidation followed by a regio-and stereoselective aminolysis of vinyl epoxide 11 to give piperidine 12.

📜 SIMILAR VOLUMES

Enantiopure 2,3-dihydro-4-pyridones as s
Enantiopure 2,3-dihydro-4-pyridones as synthetic intermediates: asymmetric synthesis of 1-deoxynojirimycin
✍ Daniel L Comins; Alan B Fulp 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 57 KB

An asymmetric synthesis of 1-deoxynojirimycin (2) mediated by a chiral auxiliary is reported. The dihydropyridone 4 was converted to diol 11 in three steps by acetoxylation, hydrolysis, and stereoselective reduction. Dihydroxylation of 11 followed by catalytic reduction afforded 2.

ChemInform Abstract: Enantiopure 2,3-Dih
ChemInform Abstract: Enantiopure 2,3-Dihydro-4-pyridones as Synthetic Intermediates: Asymmetric Synthesis of 1-Deoxynojirimycin.
✍ Daniel L. Comins; Alan B. Fulp 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 2 views

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