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内炔丙基二醇的酶促动力学拆分。第一部分:一种合成(S)-戊-2-炔-1,4-二醇的新方法,(S)-戊-2-炔-1,4-二醇是一种来自小蘑菇的天然产物。

Enzymatic kinetic resolution of internal propargylic diols. Part I: a new approach for the synthesis of (S)-pent-2-yn-1,4-diol, a natural product from Clitocybe catinus.

作者信息

Ferreira Jeiely G, Princival Cleverson R, Oliveira Dyego M, Nascimento Renata X, Princival Jefferson L

机构信息

Departamento de Química Fundamental, Universidade Federal de Pernambuco - UFPE, Av. Jornalista Aníbal Fernandes S/N, Cidade Universitária, CEP: 50740-560, Recife, PE, Brasil.

出版信息

Org Biomol Chem. 2015 Jun 21;13(23):6458-62. doi: 10.1039/c5ob00386e. Epub 2015 May 15.

Abstract

Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.

摘要

内双取代炔丙基二醇在CAL-B催化下进行酶促动力学拆分。采用两轮顺序酶促动力学拆分(EKR),以高对映体比例(E>200)得到单乙酰氧基和双乙酰氧基炔丙基产物。高效拆分得到的手性8b被用于简洁合成(S)-1b,(S)-1b是一种由真菌棒孢小皮伞产生的光学活性天然产物。

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