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Total Syntheses of (+)‐Valiolamine and (–)‐1‐ epi ‐Valiolamine from Naturally Abundant (–)‐Shikimic Acid
Author(s) -
Quan Na,
Nie LiangDeng,
Zhu RuiHeng,
Shi XiaoXin,
Ding Wei,
Lu Xia
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300804
Subject(s) - shikimic acid , chemistry , yield (engineering) , shikimate pathway , stereochemistry , organic chemistry , total synthesis , biosynthesis , enzyme , materials science , metallurgy
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.