TY - JOUR
T1 - Pyrylium salts in polyene natural product synthesis
T2 - Organometallic additions to 4-methylpyrylium tetrafluoroborate
AU - Taylor, Richard J.K.
AU - Hemming, Karl
AU - De Medeiros, Edna Faria
PY - 1995/12/1
Y1 - 1995/12/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049085572&partnerID=8YFLogxK
U2 - 10.1039/P19950002385
DO - 10.1039/P19950002385
M3 - Article
AN - SCOPUS:37049085572
SP - 2385
EP - 2392
JO - Journal of the Chemical Society, Perkin Transactions 2
JF - Journal of the Chemical Society, Perkin Transactions 2
SN - 0300-922X
IS - 19
ER -