400723-13-9Relevant academic research and scientific papers
A new 1,5- to 1,11-carbonyl transposition protocol involving ketene dithioacetal chemistry: An efficient polyene synthesis
Asokan,Shukla,Kumar,Ila,Junjappa
, p. 937 - 947 (2007/10/03)
An efficient strategy for alternative 1,5-, 1,7-, 1,9- and 1,11- carbonyl transposition has been developed via 1,2-reductive or alkylative addition to 5,5-bis(methylthio)-2,4-pentadienals 3a-b, 7,7-bis(methylthio)-2,4,6-heptatrienones 5,9,9-bis(methylthio)-2,4,6,8-nonatetraenones 8 and 11,11-bis(methylthio)-2,4,6,8,10-undecapentaenones 11 followed by BF3,Et2O induced methanolysis of the resulting carbinols to the corresponding polyene esters. The synthesis of the novel polyene aldehydes 3a-b, 7a-b, 10b and polyenones 5, 8, 11 precursors has also been described following iterative Vielsmeier-Haack reaction and aldol condensation.
