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Synlett 2000; 2000(1): 122-124
DOI: 10.1055/s-2000-6433
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A Short and Efficient Synthesis of (-)-4a,5-Dihydrostreptazolin

Janine Cossy* , Isabelle Pévet, Christophe Meyer
  • *Laboratoire de Chimie Organique, associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France; Fax +33 1 40 79 46 60; E-mail: janine.cossy@espci.fr, christophe.meyer@espci.fr
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Publication Date:
31 December 2000 (online)

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(-)-4a,5-Dihydrostreptazolin has been synthesized in 9 steps from d-glyceraldehyde acetonide. Key steps include a diastereoselective addition of a vinylic Grignard reagent onto an imine, a ring-closing metathesis and a highly stereoselective enyne radical-mediated cyclization.

(-)-4a,5-dihydrostreptazolin - total synthesis - ring-closing metathesis - radical cyclization - d-glyceraldehyde acetonide