Beilstein J. Org. Chem.2018,14, 1668–1692, doi:10.3762/bjoc.14.143
; epoxidethiolysis; β-hydroxy sulfides; sulfur-containing natural products; Review
1. Introduction
Organosulfur compounds are widely distributed in nature, with marine organisms being the richest sources of these, since sulfur, as the sulfate ion, is the second most abundant anion in sea water after
notable; this was the first enantioselective thiolysis of a meso-epoxide in pure water as a solvent. Since this report, several epoxidethiolysis reactions in water have been reported and are part of several reviews [45][46].
Schneider and co-workers reported the same scandium–bipyridine complex as
yields the required leukotriene [84][85][86][87][88][89][90][91][92][93][94][95][96][97][98].
Epoxidethiolysis to furnish β-hydroxy sulfides was also elegantly utilized by Kishi and co-workers in their landmark synthesis of pteriatoxins and their diastereomers [99]. The advanced intermediate 122 was
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Graphical Abstract
Figure 1:
Some sulfur-containing natural products.