128291-72-5Relevant academic research and scientific papers
Control of stereochemistry in an intramolecular Diels-Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol
Bush, Edward J.,Jones, David W.
, p. 3531 - 3536 (2007/10/03)
Thermolysis of 4a (X = H) gives 6a and 6b (X = H) in a ratio of 1:4 whereas 4b (X = SO2Ph) gives more of the trans-ring junction product 6a (X = SO2Ph) suitable for the synthesis of pisiferol [ratio 6a:6b (X = SO2Ph) = 1.5:1]. Base catalysed elimination of the phenylsulfonyl group from 6a (X = SO2Ph) gives 18 which is hydrogenated to 6a (X = H), an intermediate in the synthesis of pisiferol. Both 6a and 6b (X = SO2Ph) have ring B in a half-boat conformation.
Synthesis of pisiferol revisited; control of stereochemistry in an intramolecular Diels-Alder reaction
Bush, Edward J.,Jones, David W.,Thornton-Pett, Mark
, p. 9755 - 9758 (2007/10/02)
Thermolysis of 4(X=H) gives 6a and 6b(X=H) in a ratio of 1:4 whereas 4 (X=SO2Ph) gives more of trans-ring junction product 6a(X=SO2Ph) suitable for the synthesis of pisiferol [ratio 6a: 6b(X=S)2Ph) = 1.5:1].
