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- Title
Total Syntheses of (+)-Valiolamine and (-)-1- epi-Valiolamine from Naturally Abundant (-)-Shikimic Acid.
- Authors
Quan, Na; Nie, Liang‐Deng; Zhu, Rui‐Heng; Shi, Xiao‐Xin; Ding, Wei; Lu, Xia
- Abstract
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.
- Subjects
SHIKIMIC acid; CHEMICAL yield; DRUG design; GLYCOSIDASES; STREPTOMYCES hygroscopicus; AROMATIC compounds; TRIFLUOROACETIC acid; METHANESULFONATES
- Publication
European Journal of Organic Chemistry, 2013, Vol 2013, Issue 28, p6389
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201300804