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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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Published in: | Tetrahedron 2004-09, Vol.60 (37), p.8199-8205 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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 |
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ISSN: | 0040-4020 1464-5416 |
DOI: | 10.1016/j.tet.2004.06.112 |