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Synlett 1995; 1995(5): 452-454
DOI: 10.1055/s-1995-4982
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Chelate Controlled Intramolecular Diels-Alder Reaction as Key for Synthesis of a Dihydromevinolin Precursor

Jürgen Schnaubelt, Hans-Ulrich Reissig*
  • *Institut für Organische Chemie der Technischen Universität Dresden, Mommsenstrasse 13, D-01062 Dresden, Germany
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Publication Date:
31 December 2000 (online)

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Trienone 7 was available in reasonable overall yield from enone 8 via siloxycyclopropane derivatives 9 and 10. SnCl4 promoted intramolecular Diels-Alder reaction of 7 afforded trans-6b as major component which was stereoselectively converted by standard procedures into intermediate 5 bearing six stereogenic centres as required for the dihydromevinolin core.

Diels-Alder-Reaction intramolecular - Dihydromevinolin - Trienone - Chelate-Control - Lewis Acid

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