MNBA-mediated β-lactone formation: mechanistic studies and application for the asymmetric total synthesis of tetrahydrolipstatin

The Journal of Organic Chemistry
Isamu ShiinaTakashi Katoh

Abstract

Various β-lactones were prepared from β-hydroxycarboxylic acids by intramolecular dehydration condensation using MNBA, an effective coupling reagent, along with a nucleophilic catalyst. The transition state that provides the desired 4-membered ring model system is disclosed by density functional theory (DFT) calculations, and the structural features of the transition form are discussed. This method was successfully applied to the asymmetric total synthesis of tetrahydrolipstatin (THL), an antiobestic drug used in clinical treatment to inhibit the activity of pancreatic lipase.

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Citations

Apr 16, 2014·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Isamu Shiina
Dec 2, 2017·Chemistry : a European Journal·Feipeng LiuQinghua Bian
Mar 29, 2018·The Journal of Organic Chemistry·Lena Kämmler, Martin E Maier
May 21, 2014·The Journal of Organic Chemistry·Manas Das, Donal F O'Shea
Apr 22, 2015·The Journal of Organic Chemistry·Christian A MalapitAmy R Howell
Jul 28, 2019·The Journal of Organic Chemistry·Jian-Xing Xu, Xiao-Feng Wu

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