(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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© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

(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.