通过双向霍纳-沃兹沃思-埃蒙斯缩合反应合成不稳定的全反式-7,8,7',8'-双炔基类胡萝卜素。

Synthesis of labile all-trans-7,8,7',8'-bis-acetylenic carotenoids by bi-directional Horner-Wadsworth-Emmons condensation.

作者信息

Vaz Belén, Fontán Noelia, Castiñeira Marta, Álvarez Rosana, de Lera Ángel R

机构信息

Department of Organic Chemistry and Center for Biomedical Research (CINBIO), IBIV, Universidade de Vigo, 36310 Vigo, Spain.

出版信息

Org Biomol Chem. 2015 Mar 14;13(10):3024-31. doi: 10.1039/c4ob02144d.

DOI:10.1039/c4ob02144d

PMID:25622142

Abstract

A new stereoselective synthesis of the C40-bis-acetylenic carotenoids all-trans-(3R,3'R)-alloxanthin and all-trans-3,4,7,8,3',4',7',8'-octadehydro-β,β-carotene, both compounds featuring a stereochemically labile C7-C10 enyne, based on a bi-directional Horner-Wadsworth-Emmons (HWE) reaction of a C15-phosphonate and a central C10-dialdehyde, is reported. The triene unit of the latter fragment was synthesized using the acyclic metathesis/dimerization reaction.

摘要

报道了一种新的立体选择性合成C40-双炔类胡萝卜素全反式-(3R,3'R)-别藻黄素和全反式-3,4,7,8,3',4',7',8'-八脱氢-β,β-胡萝卜素的方法，这两种化合物都具有立体化学不稳定的C7-C10烯炔，该方法基于C15-膦酸酯与中心C10-二醛的双向霍纳尔-沃兹沃思-埃蒙斯（HWE）反应。后一个片段的三烯单元是使用开环复分解/二聚反应合成的。