Reactivity of (3-chloro-2-methylenecycloalkyl)pallladium Chloride Dimers: A Palladium Mediated Ring Homologation--Functionalization Approach to the AR-7-7 Skeleton of Colchicine

Authors

William Donaldson, Marquette UniversityFollow
Daniel John Stepuszek, Marquette University
James A. Gruetzmacher, Marquette University

Document Type

Article

Language

eng

Publication Date

1990

Publisher

Elsevier

Source Publication

Tetrahedron

Source ISSN

0040-4020

Abstract

A palladium mediated ring homologation--functionalization approach to the Ar-7-7 tricyclic skeleton of colchicine from 1-arylcyclohexenes is described. This methodology involves the chloropalladation of 1-aryl-7-methylenebicyclo[4.1.0]heptanes to afford aryl substituted (3-chloro-2-methylenecycloheptyl)palladium chloride dimers. Reaction of the π-allyl complexes with one equivalent of malonate anion gives a cycloheptadiene product. Subsequent reduction and intramolecular acylation yields the Ar-7-7 skeleton.

Comments

Tetrahedron, Vol. 46, No. 7 (1990): 2273-2280. DOI.

Recommended Citation

Donaldson, William; Stepuszek, Daniel John; and Gruetzmacher, James A., "Reactivity of (3-chloro-2-methylenecycloalkyl)pallladium Chloride Dimers: A Palladium Mediated Ring Homologation--Functionalization Approach to the AR-7-7 Skeleton of Colchicine" (1990). Chemistry Faculty Research and Publications. 862.
https://epublications.marquette.edu/chem_fac/862