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EnglishAbstract—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.
| Titolo: | Atom Tranfer Radical Cyclization (ATRC) applied to a chemo-enzymatic synthesis of Quercus Lactones |
| Autori: | |
| Data di pubblicazione: | 2007 |
| Rivista: | |
| 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. |
| Handle: | http://hdl.handle.net/11368/1699348 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tetasy.2007.02.012 |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
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