Atom transfer radical cyclization (ATRC) applied to a chemoenzymatic synthesis of Quercus lactones

F Felluga, C Forzato, F Ghelfi, P Nitti, G Pitacco…

Index: Felluga, Fulvia; Forzato, Cristina; Ghelfi, Franco; Nitti, Patrizia; Pitacco, Giuliana; Pagnoni, Ugo Maria; Roncaglia, Fabrizio Tetrahedron Asymmetry, 2007 , vol. 18, # 4 p. 527 - 536

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Citation Number: 38

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 ...