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Asymmetric synthesis of (+)-1-deoxynojirimycin and (+)-castanospermine
KTH, Superseded Departments, Chemistry.
2003 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 59, no 8, p. 1293-1299Article in journal (Refereed) Published
Abstract [en]

Asymmetric total syntheses of (+)-1-deoxynojirimycin (1) and (+)-castanospermine (2) are described. Starting from diene 3, the required absolute stereochemistry is introduced by an asymmetric hydroxylation followed by epoxidation. An intramolecular cyclization of amine 17 gives access to the corresponding tetrasubstituted piperidine 18, which is a precursor to compounds 1 and 2. (+)-Deoxynojirimicyn (1) was obtained in 36% yield over 11 steps from diene 3, while (+)-castanospermine (2) was achieved in 13% after 19 steps from the same starting material.

Place, publisher, year, edition, pages
2003. Vol. 59, no 8, p. 1293-1299
Keywords [en]
amino alcohols, asymmetric synthesis, alkaloids, allylic 4-methoxybenzoates, castanospermine, dihydroxylation, deoxynojirimycin, derivatives, glucosidase, inhibition
Identifiers
URN: urn:nbn:se:kth:diva-22256ISI: 000181019900019OAI: oai:DiVA.org:kth-22256DiVA, id: diva2:340954
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10 Last updated: 2017-12-12Bibliographically approved

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