Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji-Trost Allylation

Michael Popadynec; Helen Gibbard; J Stephen Clark

doi:10.1021/acs.orglett.0c01238

Bidirectional Synthesis of the IJK Fragment of Ciguatoxin CTX3C by Sequential Double Ring-Closing Metathesis and Tsuji-Trost Allylation

Org Lett. 2020 May 1;22(9):3734-3738. doi: 10.1021/acs.orglett.0c01238. Epub 2020 Apr 19.

Authors

Michael Popadynec¹, Helen Gibbard¹, J Stephen Clark¹

Affiliation

¹ School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow, G12 8QQ, United Kingdom.

Abstract

A novel four-step bidirectional strategy has been used to synthesize the IJK fragment of the marine polyether natural product CTX3C from a simple monocyclic precursor in a concise and efficient manner. The four-step bidirectional sequence involves ring-closing metathesis, alcohol oxidation, enol carbonate formation, and palladium-mediated Tsuji-Trost allylation.

Publication types

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