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Asymmetric synthesis of 1-deoxynojirimycin and its congeners from a common chiral building block |
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| Authors: | Hiroki Takahata Yasunori Banba Hideo Nemoto Isao Adachi |
| Institution: | a Faculty of Pharmaceutical Sciences, Tohoku Pharmaceutical University, Sendai 981-8558, Japan b Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama 930-0194, Japan c Department of Hospital Pharmacy, Toyama Medical and Pharmaceutical University, Toyama 930-0194, Japan |
| Abstract: | 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. |
| Keywords: | Iminosugars Garner aldehyde Asymmetric synthesis |
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