The natural fragrances (+)-trans whisky lactone 2 and (+)-trans cognac lactone 4, together with a minor amount of their ()-cis stereoisomers, were prepared in 50% and 42% overall yield, respectively, starting from racemic 1-hepten-3-ol (±)-5 and 1-octen-3-ol(±)-6. The procedure involved first the enantioconvergent, lipase mediated transformation of the secondary allylic alcohols deriveddichloroacetates (±)-7 and (±)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transitionmetal catalyzed atom transfer process.
Atom Tranfer Radical Cyclization (ATRC) applied to a chemo-enzymatic synthesis of Quercus Lactones / Felluga, F; Forzato, C; Ghelfi, Franco; Nitti, P; Pitacco, G; Pagnoni, Ugo Maria; Roncaglia, Fabrizio. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 18:4(2007), pp. 527-536. [10.1016/j.tetasy.2007.02.012]
Atom Tranfer Radical Cyclization (ATRC) applied to a chemo-enzymatic synthesis of Quercus Lactones
GHELFI, Franco;PAGNONI, Ugo Maria;RONCAGLIA, Fabrizio
2007
Abstract
The natural fragrances (+)-trans whisky lactone 2 and (+)-trans cognac lactone 4, together with a minor amount of their ()-cis stereoisomers, were prepared in 50% and 42% overall yield, respectively, starting from racemic 1-hepten-3-ol (±)-5 and 1-octen-3-ol(±)-6. The procedure involved first the enantioconvergent, lipase mediated transformation of the secondary allylic alcohols deriveddichloroacetates (±)-7 and (±)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transitionmetal catalyzed atom transfer process.
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