101347-23-3Relevant academic research and scientific papers
A new approach to retinoids via organometallic addition to pyrylium salts
Hemming,De Medeiros,Taylor
, p. 2623 - 2624 (1994)
A new, concise approach to retinoid synthesis is described based on organometallic addition to pyrylium salts, the use of 4-methylpyrylium tetrafluoroborate giving 13Z-retinal which is readily isomerised to retinal itself; the corresponding unsubstituted and 4-cyclohexyl pyrylium salts are transformed into 13-H and 13-cyclohexyl retinal analogues.
Pyrylium salts in polyene natural product synthesis: organometallic additions to 4-methylpyrylium tetrafluoroborate
Taylor, Richard J. K.,Hemming, Karl,Medeiros, Edna Faria De
, p. 2385 - 2392 (2007/10/02)
The synthetic utility of organometallic additions to pyrylium salts as a procedure for the stereocontrolled preparation of 2Z,4E-dienals, and the use of these compounds in polyene natural product synthesis, is summarised.The extension of this methodology to 4-methylpyrylium tetrafluoroborate to give a new route to 3-methyl-2Z,4E-dienals via a six-carbon organometallic homologation procedure is then described.Finally, the utilisation of this methodology to provide a concise synthetic approach to 13Z-retinal, retinal and a range of retinal analogues is then elaborated.
