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Synlett 1996; 1996(11): 1029-1035
DOI: 10.1055/s-1996-5657
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Our Tactics in Ring Enlargement - Construction of Medium and Large Ring Compounds

Werner Tochtermann* , Philip Kraft
  • *Institut für Organische Chemie der Universität Kiel, Olshausenstraße 40, D-24098 Kiel, Germany, Fax +49(0)431/880-1558
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Publikationsdatum:
31. Dezember 2000 (online)

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This Account presents our tactics in the synthesis of medium and large ring compounds. First the application of an oxanorbornadiene → oxepine ring enlargement to the synthesis of a [6]paracyclophane, of hydroazulenes, and bridged furanosides is described. Transformations of the Diels-Alder adduct of cyclooctyne and furan led to the synthesis of (-)-muricatacin and guided our way into Fragrance Chemistry. Finally, the stereoselective synthesis of macrocyclic odorants by way of ring enlargement of cycloalkanones with chiral building blocks is highlighted.

ring enlargement - oxepines - hydroazulenes - macrocyclic odorants - chiral building blocks