Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials

Martin Kamlar; August Runemark; Ivana Císařová; Henrik Sundén

doi:10.1021/acs.orglett.0c03020

Polycyclizations of Ketoesters: Synthesis of Complex Tricycles with up to Five Stereogenic Centers from Available Starting Materials

Org Lett. 2020 Nov 6;22(21):8387-8391. doi: 10.1021/acs.orglett.0c03020. Epub 2020 Oct 20.

Authors

Martin Kamlar^{1

2}, August Runemark¹, Ivana Císařová³, Henrik Sundén^{1

4}

Affiliations

¹ Department of Chemistry and Chemical Engineering, Chalmers University of Technology, Kemivägen 10, 412 96 Gothenburg, Sweden.
² Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague 2, Czech Republic.
³ Department of Inorganic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague 2, Czech Republic.
⁴ Department of Chemistry and Molecular Biology, University of Gothenburg, Kemivägen 10, SE-412 96 Gothenburg, Sweden.

Abstract

Here we present a polycyclization of oxotriphenylhexanoates. The polycyclization is governed by electronic effects, and three major synthetic paths have been established leading to stereochemically complex tricyclic frameworks with up to five stereogenic centers. The method is compatible with an array of functional groups, allowing pharmacophoric elements to be introduced post cyclization.

Publication types

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