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 derived dichloroacetates (±)-7 and (±)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transition metal catalyzed atom transfer process.
Atom Tranfer Radical Cyclization (ATRC) applied to a chemo-enzymatic synthesis of Quercus Lactones / Felluga, Fulvia; Forzato, Cristina; F., Ghelfi; Nitti, Patrizia; Pitacco, Giuliana; U. M., Pagnoni; F., Roncaglia. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 18:(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
FELLUGA, FULVIA;FORZATO, Cristina;NITTI, PATRIZIA;PITACCO, GIULIANA;
2007-01-01
Abstract
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 derived dichloroacetates (±)-7 and (±)-8 into the corresponding homochiral (+)-7 and (+)-8, combined with their cyclization under a transition metal catalyzed atom transfer process.Pubblicazioni consigliate
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