Efficient and stereodivergent synthesis of deoxyimino sugars.
Both cis- and trans-2-substituted-1,2,3,6-tetrahydro-pyridin-3-ols have been prepared via an aldol condensation-ring-closing metathesis sequence. A stereodivergent synthesis of optionally functionalized deoxyimino sugars was achieved via asymmetric dihydroxylation or epoxidation/nucleophilic substitution of these tetrahydropyridines.
Hong
Bor-Cherng
BC
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi 621, Taiwan, ROC. chebch@ccu.edu.tw
Chen
Zhong-Yi
ZY
Nagarajan
Arumugam
A
Kottani
Rudresha
R
Chavan
Vishal
V
Chen
Wei-Hung
WH
Jiang
Yea-Fen
YF
Zhang
Shuo-Cang
SC
Liao
Ju-Hsiou
JH
Sarshar
Sepehr
S
D018360:Crystallography, X-Ray; D003837:Deoxy Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D050111:Imino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D003837:Deoxy Sugars; D050111:Imino Sugars