Abstract
The present review covers synthetic work accomplished in the oligo-tetrahydrofuran (oligo-THF) area between 1986 and July 1994. Oligo-THFs are key structural elements in the Annonaceous acetogenins, natural products with interesting biological and pharmacological activities. Nonnatural oligo-THFs possess potential applications in the field of ion binding (THF-probands) and ion transport (membrane bound ion channels made out of oligo-THFs). Described here is the current synthetic methodology to obtain oligo-THFs in a stereocontrolled manner. Emphasis is made on two approaches: intramolecular epoxide opening (epoxide-cyclization cascades) and intramolecular ether formation (multiple Williamson reactions).