A facile synthesis of 1,4-dideoxy-1,4-imino-l-ribitol (LRB) and (−)-8a-epi-swainsonine from d-glutamic acid |
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| Authors: | Xiao-Ling WangWen-Feng Huang Xin-Sheng Lei Guo-Qiang Lin |
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| Affiliation: | a Department of Chemistry and Institutes of Biomedical Sciences, Fudan University, 220 Handan Road, Shanghai 200433, China
b School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai 201203, China |
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| Abstract: | A facile synthesis of (−)-8a-epi-swainsonine 2 and 1,4-dideoxy-1,4-imino-l-ribitol (LRB) 4 has been achieved by using the versatile building block 3, which was available from cheap d-glutamic acid. The new forming stereogenic center in synthesis of 2 was constructed by highly selective reduction of the ketone 13 with Li(t-BuO)3AlH in THF (dr=95:5). |
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| Keywords: | Alkaloid Lactam Asymmetric synthesis Swainsonine LRB |
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