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Synthesis 1995; 1995(2): 115-132
DOI: 10.1055/s-1995-3883
review
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Stereoselective Synthesis of Oligo-Tetrahydrofurans

Ulrich Koert*
  • *Fachbereich Chemie der Universität Marburg, D-35032 Marburg/Lahn, Germany
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Publication History

Publication Date:
31 December 2000 (online)

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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).

polyether - oligo-tetrahydrofuran - stereoselective synthesis - epoxide-cyclization cascade - multiple Williamson reaction - Annonaceous acetogenins