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Revista de la Sociedad Química de México

Print version ISSN 0583-7693


AGUILAR, Raúl et al. A New Approach for the Synthesis of the Cyclohexene Core of Anthracyclines and Milbemycins. Rev. Soc. Quím. Méx [online]. 2000, vol.44, n.2, pp.91-96. ISSN 0583-7693.

A new synthesis of the cyclohexene core of the anthracyclines and milbemycins antibiotics is described, using 3-p-nitroben-zoyloxy-3-buten-2-one (9a) as an efficient dienophile in Diels-Alder reactions with substituted dienes. Allylic functionalization and epimerization of the cycloadducts led, in moderate overall yields, to the corresponding related cyclohexene A-rings of aclacinomycin, α- and β-rhodomycins, and the cyclohexene moiety of milbemycins β1 and E.

Keywords : Captodative olefin; Diels-Alder; cyclohexene core; anthracyclines; milbemycins.

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