Synthesis of (+)-Vitepyrroloid A and (+)-Vitepyrroloid B by Late-Stage Ni-Catalyzed C(sp2)-C(sp3) Cross-Electrophile Coupling

Martina Menger; Dieter Lentz; Mathias Christmann

doi:10.1021/acs.joc.8b00882

Synthesis of (+)-Vitepyrroloid A and (+)-Vitepyrroloid B by Late-Stage Ni-Catalyzed C(sp2)-C(sp3) Cross-Electrophile Coupling

J Org Chem. 2018 Jun 15;83(12):6793-6797. doi: 10.1021/acs.joc.8b00882. Epub 2018 May 31.

Authors

Martina Menger¹, Dieter Lentz¹, Mathias Christmann¹

Affiliation

¹ Freie Universität Berlin, Institute of Chemistry and Biochemistry , Takustrasse 3 , 14195 Berlin , Germany.

PMID: 29774741
DOI: 10.1021/acs.joc.8b00882

Abstract

A concise and scalable five-step synthesis of vitepyrroloids A and B, two cytotoxic labdane diterpenoid alkaloids from Vitex trifolia, is reported. The presented approach features a Ni-catalyzed cross-electrophile coupling between a (+)-sclareolide-derived alkyl iodide and 3-bromo-2-cyanopyrrole.