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Eleuthesides and Their Analogs: I. Synthesis of the Base Compound from Levoglucosenone Adduct with Piperylene

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY (2010)

Journal

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY

Volume 46, Issue 8, Pages 1151-1156

Publisher

MAIK NAUKA/INTERPERIODICA/SPRINGER

DOI: 10.1134/S1070428010080063

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Categories

Chemistry, Organic

Funding

Russian Foundation for Basic Research [08-03-97033-r_povolzh'e_a, NSh-1725.2008.3]

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Abstract

The Diels-Alder adduct of levoglucosenone and piperylene was converted into the corresponding oxime, and second-order Beckmann rearrangement of the latter, followed by treatment with a base, gave (1S,2R,6R)-6-(2-hydroxyethyl)-2-methylcyclohex-3-ene-1-carbaldehyde which was used in the synthesis of eleutheside analog. Conditions were found for opening of oxirane ring with formation of primary alcohol and simultaneous reduction of cyano group to aldehyde by the action of Red-Al-H(2)O.

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