Total Syntheses of (+)-Valiolamine and (-)-1-epi-Valiolamine from Naturally Abundant (-)-Shikimic Acid

Total syntheses of (+)‐valiolamine (1) and (–)‐1‐epi‐valiolamine (2) from the naturally abundant (–)‐shikimic acid are described. Ethyl 3‐epi‐5‐O‐methylsulfonyl‐shikimate (3), as the key common intermediate, was first synthesized in five steps in 74 % overall yield, and then converted into the targe...

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Bibliographic Details
Published in:European journal of organic chemistry 2013-10, Vol.2013 (28), p.6389-6396
Main Authors: Quan, Na, Nie, Liang-Deng, Zhu, Rui-Heng, Shi, Xiao-Xin, Ding, Wei, Lu, Xia
Format: Article
Language:English
Subjects:
Carbohydrates
Drug design
Inhibitors
Natural products
Total synthesis
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Summary:Total syntheses of (+)‐valiolamine (1) and (–)‐1‐epi‐valiolamine (2) from the naturally abundant (–)‐shikimic acid are described. Ethyl 3‐epi‐5‐O‐methylsulfonyl‐shikimate (3), as the key common intermediate, was first synthesized in five steps in 74 % overall yield, and then converted into the targets 1 and 2 in seven steps in 48 and 41 % overall yield, respectively. Total syntheses of (+)‐valiolamine (1) and (–)‐1‐epi‐valiolamine (2) from (–)‐shikimic acid are described. Ethyl 3‐epi‐5‐O‐methylsulfonyl‐shikimate (3), as the key common intermediate, was first synthesized in five steps (74 % yield) and then converted into the targets in seven steps in 48 and 41 % overall yield, respectively.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300804