Synthesis of (3aR, 4S, 5R, 6aS)-5-hydroxy-4-(hydroxymethyl) hexahydro-2H-cyclopenta[b] furan-2-one

Ze Wang Feng*, Xin Qi Zhao, Cheng Hui Sun, Hua Bi

*此作品的通讯作者

科研成果: 期刊稿件文章同行评审

1 引用 (Scopus)

摘要

Racemic 3, 3-dichloro-3, 3a, 6, 6a-tetrahydro-2H-cyclopenta[b] furan-2-one (4) is prepared in a yield of 65.3% from cyclopentadiene and dichloroacetyl chloride through a process of cycloaddition and Baeyer-Villiger oxidation. Through the resolution of racemic 4 by optically active phenethylamine (PEA) and Prins reaction with polyformaldehyde followed by the hydrolysis without separation, (3aR, 4S, 5R, 6aS)-3,3-dichloro-5-hydroxy-4-(hydroxymethyl) hexahydro-2H-cyclopenta[b] furan-2-one (6) is obtained in a 26.4% yield. (3aR, 4S, 5R, 6aS)-5-Hydroxy-4-(hydroxylmethyl) hexahydro-2H-cyclopenta [b] furan-2-one (2) is prepared in a 96.4% yield from 6 via the reduction with zinc dust.

源语言英语
页(从-至)60-63
页数4
期刊Xiandai Huagong/Modern Chemical Industry
28
5
出版状态已出版 - 5月 2008

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