18432-37-6Relevant articles and documents
Improved synthesis of γ-lactones from cyclopropyl cyanoesters
Patel, Nandini C.,Schwarz, Jacob B.,Islam, Khondaker,Miller, Whitney,Tran, Tuan P.,Wei, Yunjing
, p. 2209 - 2215 (2011/07/07)
Cyclopropyl cyanoesters 2 were reliably converted to c-lactones 4 on treatment with aqueous sulfuric acid. The cyanoesters could be easily prepared from ketones or aldehydes in two steps, making this process particularly attractive from an efficiency standpoint. Copyright
A mild biosynthesis of lactones via enantioselective hydrolysis of hydroxynitriles
Pollock, Julie A.,Clark, Karen M.,Martynowicz, Bethany J.,Pridgeon, Matthew G.,Rycenga, Matthew J.,Stolle, Kristen E.,Taylor, Stephen K.
, p. 1888 - 1892 (2008/02/12)
We have developed a biocatalytic method to produce lactones and related compounds via the enzymatic hydrolysis of γ- and β-hydroxynitriles. The synthesis is a mild, general, and environmentally friendly way to enantioselectively hydrolyze nitriles with commercially available nitrilase enzymes. The synthesis of four pheromones is demonstrated via a one-step method.
Synthesis of natural (-)-hamigeran B
Clive, Derrick L.J.,Wang, Jian
, p. 7731 - 7733 (2007/10/03)
Alkylation of lactam 10, first with iodide 15 and then with MeI, gave mainly (18:1) lactam 18. This was converted by treatment with t-BuLi and then with aqueous base into enone 4, which was elaborated into (-)-hamigeran B. A key feature of the last part of the synthesis is the use of t-BuMe 2Si-groups (as in intermediate 24) both to direct hydrogenation from the appropriate face and to protect the benzylic C-O bond from hydrogenolysis.