122674-58-2Relevant academic research and scientific papers
Carbohydrates to Carbocycles: A Synthesis of (-)-α-Pipitzol
Pak, Helen,Canalda, Isabel Iriepa,Fraser-Reid, Bert
, p. 3009 - 3011 (2007/10/02)
A 2-deoxy-3-keto sugar derived from methyl α-D-mannopyranoside has been processed to give a multibranched-chain sugar which undergoes serial radical cyclization, affording a pyranosidodiquinane as the key intermediate.The diquinane moiety represents the B
Serial Radical Cyclization of Branched Carbohydrates. 2. Claisen Rearrangement Routes to Muliply Substituted Pyranoside Diquinanes
Pak, Helen,Dickson, John K.,Fraser-Reid, Bert
, p. 5357 - 5364 (2007/10/02)
Pyranosidic diquinanes, which may be prepared by serial radical cyclization of suitably functionalized alkyl residues at C2 and C3, are potential precursors for polyquinane synthesis.The residues at C3 are installed via a Claisen rearrangement, and it is therefore possible to obtain more highly substituted diquinane synthons by incorporating methyl residues at the appropriate sites in the precursors.The consequences of these substituents on the stereoselectivity of the Claisen rearrangement have been examined.
