35219-73-9Relevant articles and documents
Preparation of diallyl ketals
Brogan,Richard,Zercher
, p. 587 - 593 (1995)
A general method for the preparation of diallyl acetals and ketals is reported. The reaction is performed well below room temperature, thereby eliminating any competing Claisen rearrangement. These mild reaction conditions also facilitate ketal formation on methyl levulinate 1 with no transesterification.
The Convergent Synthesis of Polyether Ionophore Antibiotics: An Approach to the Synthesis of the Monensin Tetrahydropyran-Bis(tetrahydrofuran) via the Ester Enolate Claisen Rearrangement and Reductive Decarboxylation
Ireland, Robert E.,Norbeck, Daniel W.,Mandel, Gretchen S.,Mandel, Neil S.
, p. 3285 - 3294 (2007/10/02)
The monensin tetrahydropyran equivalent 22 is prepared from D-fructose and then joined to the monensin bis(tetrahydrofuran) equivalent 24a via the ester enolate Claisen rearrangement.Methodology for the radical induced, reductive decarboxylation of the resulting acid 26a is described.Anomeric stabilization of the intermediate tetrahydrofuran-2-yl radical is an important factor in the stereochemical outcome of this process.Reduction of 1-chloro-2,3-O-isopropylidene furanoid and pyranoid carbohydrate derivatives with lithium di-tert-butylbiphenyl affords the corresponding glycals in high yield.