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Synlett 1994; 1994(12): 998-1000
DOI: 10.1055/s-1994-34982
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New Synthetic Approach to the Western Part C10-C15 of (±)-Des-Epoxy-Rosaramycin

Patrick Le Ménez* , Isabelle Berque, Valérie Fargeas, Janick Ardisson, Ange Pancrazi
  • *Laboratoire de Chimie des Substances Thérapeutiques Naturelles, (CNRS, BIOCIS, URA 1843), Centre d'Etudes Pharmaceutiques, 92290, Châtenay-Malabry, France.
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Publication Date:
22 March 2002 (online)

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A new route to (5E,7E,3R*,4S*)-4, 6-dimethyl-8-tri-n-butylstannyl-octa-5,7-dien-3-ol 5 which represents the western part C10-C15 of the macrocyclic antibiotic (±)-des-epoxy-rosaramycin I, was explored. Direct model catalytic palladium coupling reaction between (3E)-4-iodo-pent-3-en-1-ol 8 and (E)-1,2bis (tri-n-butylstannyl) ethylene gave (3E,5E )-4-methyl-6-tributylstannyl-hex-3,5-dien-1-ol 4 in 36% yield. Stannyl cupration performed on the (5E,3R*,4S*)-4,6-dimethyl-oct-5-en-7-yn-3-ol 15 led in high yield to the expected stannyl diene 5.