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Abstracts of Congress of Heterocyclic Chemistry | Regular issue | Vol 14, No. 10, 1980, pp.1615-1630
Published online, 1st January, 1970
DOI: 10.3987/R-1980-10-1615
Preparation and Use of Nitrogen- or Sulphur containing Heterocycles in Organic Synthesis

Wolfgang Oppolzer*

*Department of Organic Chemistry, Laboratory fo Crystallography, University of Geneva, 30, quai Ernest Ansermet, 1211 Geneva 4, Switzerland

Abstract

The utility of intramolecular cycloadditions of ortho-quinodimethanes for the synthesis of complex polycyclic molecules is illustrated: 1) by the stereoselective synthesis of the natural alkaloid (±)-chelidonine starting from a benzocyclobutene; 2) by the efficient preparation of various polycyclic carbon skeletons using 1,3-dihydroisothianaphthen-2,2-dioxide as a simple building block. Furthermore, the total syntheses of the ergolines chanoclavine I and isochanoclavine I, exploiting a regio- and stereo-selective intramolecular nitrone-olefin-addition, is described.