A Metathesis Approach for the Preparation of Polyhydroxylated Compounds as Head Groups in Surfactant Synthesis

Abstract

Starting from methyl‐α‐D‐glucopyranoside, an efficient protocol for the preparation of polyhydroxylated surfactant head‐groups is demonstrated and applied in the synthesis of a typical surfactant. The key transformation is a metathesis reaction between two monosaccharide residues to afford an octahydroxydecen. The importance of a strategic protecting‐group constellation for a successful metathesis reaction is also investigated. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

Ring‐Closing Metathesis in the Synthesis of BC Ring‐Systems of Taxol

“…The structure of this cyclooctene was confirmed by X-ray analysis. [17] The decomposition or low reactivity [18] or occasional loss of methylene [19] in ring-closing metathesis reactions in the presence of a diol were not observed in our case.…”

Applications of Yamaguchi Method to Esterification and Macrolactonization in Total Synthesis of Bioactive Natural Products

“…[24] The Yamaguchi method is particularly effective in the synthesis of macrolactones, has found eminent use in the regioselective synthesis of highly functionalized esters. [25,26] This esterification methodology was successfully applied to the synthesis of Lux-S aspartic acid inhibitor (Scheme 3) [24] as shown below:-…”