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Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block

A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5- trans-oriented azasugars such as 1-deoxynojirimycin ( 1 ) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical tes...

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Bibliographic Details
Published in:Tetrahedron 2004-09, Vol.60 (37), p.8199-8205
Main Authors: Takahata, Hiroki, Banba, Yasunori, Sasatani, Mayumi, Nemoto, Hideo, Kato, Atsushi, Adachi, Isao
Format: Article
Language:English
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Summary:A new, promising chiral building block 9 for the synthesis of 1-deoxy-4,5- trans-oriented azasugars such as 1-deoxynojirimycin ( 1 ) was prepared in only four steps from the Garner aldehyde 10 using catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In practical test, the first synthesis of all four isomers ( 1 and 6- 8 ) of trans-4,5-orientated 1-deoxyiminosugars using 9 as a common chiral building block was demonstrated. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2004.06.112