Total Syntheses of (+)‐Valiolamine and (–)‐1‐ epi ‐Valiolamine from Naturally Abundant (–)‐Shikimic Acid | Zendy

Quan Na | Zendy; Nie LiangDeng | Zendy; Zhu RuiHeng | Zendy; Shi XiaoXin | Zendy; Ding Wei | Zendy; Lu Xia | Zendy

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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.

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