A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

Ruben L H Andringa; Niels A W de Kok; Arnold J M Driessen; Adriaan J Minnaard

doi:10.1002/anie.202104759

A Unified Approach for the Total Synthesis of cyclo-Archaeol, iso-Caldarchaeol, Caldarchaeol, and Mycoketide

Angew Chem Int Ed Engl. 2021 Aug 2;60(32):17497-17503. doi: 10.1002/anie.202104759. Epub 2021 Jun 4.

Authors

Ruben L H Andringa¹, Niels A W de Kok², Arnold J M Driessen², Adriaan J Minnaard¹

Affiliations

¹ Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.
² Department of Molecular Microbiology, University of Groningen, Nijenborgh 7, 9747 AG, Groningen, The Netherlands.

Abstract

Ir-catalyzed asymmetric alkene hydrogenation is presented as the strategy par excellence to prepare saturated isoprenoids and mycoketides. This highly stereoselective synthesis approach is combined with an established ¹³ C-NMR method to determine the enantioselectivity of each methyl-branched stereocenter. It is shown that this analysis is fit for purpose and the combination allows the synthesis of the title compounds with a significant increase in efficiency.

Keywords: Archaea; asymmetric hydrogenation; lipids; membrane spanning; metathesis.

Publication types

Research Support, Non-U.S. Gov't