O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Suvi Holmstedt; Alexander Efimov; Nuno R Candeias

doi:10.1021/acs.orglett.1c00755

O,O-Silyl Group Migrations in Quinic Acid Derivatives: An Opportunity for Divergent Synthesis

Org Lett. 2021 Apr 16;23(8):3083-3087. doi: 10.1021/acs.orglett.1c00755. Epub 2021 Apr 7.

Authors

Suvi Holmstedt¹, Alexander Efimov¹, Nuno R Candeias^{1

2}

Affiliations

¹ Faculty of Engineering and Natural Sciences, Tampere University, Korkeakoulunkatu 8, 33101 Tampere, Finland.
² LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal.

PMID: 33826343
DOI: 10.1021/acs.orglett.1c00755

Abstract

The O,O-silyl group migrations on a quinic acid-derived cyclitol have been studied, and the ease of migration was observed to be dependent on the silicon substituents and reaction conditions. Conditions were found to improve the formation of a main isomer during the O,O-silyl group migrations that could be integrated into the formal synthesis of vitamin D receptor modulator VS-105 and in the first total synthesis of a metabolite from the African ant Crematogaster nigriceps.

Publication types

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