Issue 23, 2015
From the journal:

Organic & Biomolecular Chemistry

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†

Jeiely G. Ferreira,a   Cleverson R. Princival,b   Dyego M. Oliveira,a   Renata X. Nascimentoa  and  Jefferson L. Princival*a  

* Corresponding authors

a Departamento de Química Fundamental, Universidade Federal de Pernambuco - UFPE, Av. Jornalista Aníbal Fernandes S/N, Cidade Universitária, Recife, PE, Brasil
E-mail: princivalj@yahoo.com.br

b Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo-USP, Av. Prof. Lineu Prestes 748, Butantã, São Paulo, SP, Brasil

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.

Graphical abstract: 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

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Article information

DOI
https://doi.org/10.1039/C5OB00386E
Article type
Communication
Submitted
25 Feb 2015
Accepted
28 Apr 2015
First published
29 Apr 2015

Org. Biomol. Chem., 2015,13, 6458-6462

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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

J. G. Ferreira, C. R. Princival, D. M. Oliveira, R. X. Nascimento and J. L. Princival, Org. Biomol. Chem., 2015, 13, 6458 DOI: 10.1039/C5OB00386E

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