Total Syntheses of (+)‐Valiolamine and (–)‐1‐epi‐Valiolamine from Naturally Abundant (–)‐Shikimic Acid. Issue 28 (15th August 2013)

• Record Type: Journal Article
• Authors: Quan, Na; Nie, Liang‐Deng; Zhu, Rui‐Heng; Shi, Xiao‐Xin; Ding, Wei; Lu, Xia
• Is Part Of: European journal of organic chemistry. Issue 28(2013)
• Page Start: 6389
• Page End: 6396
• Publication Date: 2013-08-15
• Subjects: Total synthesis -- Drug design -- Natural products -- Carbohydrates -- Inhibitors; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300804
• Languages: English
• ISSNs: 1434-193X

Abstract

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 targets1 and2 in seven steps in 48 and 41 % overall yield, respectively. Abstract : 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.