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Improved Stereoselective Syntheses of (+)‐Valiolamine and (+)‐Valienamine Starting from (–)‐Shikimic Acid
Author(s) -
Li Fenglei,
Ding Wei,
Quan Na,
Wu Jiajia,
He Yungang,
Zhu Xingliang,
Shi Xiaoxin,
Zhao Jianhong
Publication year - 2017
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201600935
Subject(s) - shikimic acid , chemistry , stereoselectivity , stereochemistry , organic chemistry , catalysis
Abstract Improved stereoselective syntheses of the target compounds (+)‐valiolamine 1 and (+)‐valienamine 2 starting from naturally abundant (–)‐shikimic acid are described. A common key intermediate compound 7 was first synthesized from (–)‐shikimic acid in 9 steps. The compound 7 was then converted to (+)‐valiolamine 1 in 3 steps, and was also converted to (+)‐valienamine 2 in 4 steps. In summary, (+)‐valiolamine 1 and (+)‐valienamine 2 were synthesized from (–)‐shikimic acid in 12 (or 13) steps in 40% and 39% overall yields, respectively. The present syntheses are more practical and might be important for the potential industrial preparations of pharmaceutically valuable (+)‐valiolamine 1 and (+)‐valienamine 2 .