(Stannyl)Vinyl Cuprate in the Synthesis of the Western C10-C15-Fragment of (±)-Des-Epoxy-Rosaramycin

Patrick Le Ménez; Nadine Firmo; Valérie Fargeas; Janick Ardisson; Ange Pancrazi

doi:10.1055/s-1994-23072

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Synlett 1994; 1994(12): 995-997
DOI: 10.1055/s-1994-23072

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(Stannyl)Vinyl Cuprate in the Synthesis of the Western C₁₀-C₁₅-Fragment of (±)-Des-Epoxy-Rosaramycin

Patrick Le Ménez^* , Nadine Firmo, 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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1,2-Metallate rearrangements were performed on (2R*,3S*)-2-ethyl-3-methyl-5-lithio-2,3-dihydrofuran 3b, with different cyanocuprates, to deliver after further methylation, (3R*,4S*,5E)-4-methyl-6-(tri-n-butylstannyl)-hept-5-en-3-ol 13 or (3R*,4S*,5E,7E)-4,6-dimethyl-octa-8-(tri-n-butylstannyl)-5,7-dien-3-ol 1 which represents the western part C₁₀-C₁₅ of (±)-des-epoxy-rosaramycin I.

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