129611-92-3Relevant articles and documents
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.
OXOKETENE DITHIOACETALS AS VERSATILE SYNTHONS FOR ALTERNATIVE 1,3 TO 1,11 CARBONYL TRANSPOSITIONS: A NEW POLYENE SYNTHESIS
Chandrasekharam, Malapaka,Asokan, Chitoorthekkathil V.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 1763 - 1766 (2007/10/02)
A model strategy for 1,7 to 1,11 carbonyl transpositions involving 1,2 addition of sodium borohydride or Grignard reagents to polyenyl oxoketene dithioacetals 8 obtained by condensation of bis(methylthio)polyenals 1-3 with active methylene ketones, followed by borontrifluoride etherate catalyzed methanolysis of the resulting polyenyl carbinol acetals 9 to give 1,n transposed polyene esters 10 has been described.