81886-43-3Relevant academic research and scientific papers
Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence
Kemme, Susanne T.,?mejkal, Tomá?,Breita, Bernhard
supporting information; experimental part, p. 989 - 994 (2009/05/27)
Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].
SYNTHESIS OF QUEEN SUBSTANCE VIA THREE CARBON HOMOLOGATION ROUTE
Dhokte, U. P.,Rao, A. S.
, p. 355 - 368 (2007/10/02)
The acetoxyaldehyde 9 prepared in five steps from methylcyclohexene 4 furnished the alkylidine succinic ester 12 when reacted with diethyl diethoxyphosphinylbutanedioate 11.The ester 12 was transformed to the half ester 17, which on oxidative decarboxylation (lead tetraacetate, cupric acetate) gave a 3:1 mixture of esters 18 and 2 which was converted to the Queen Substance 1.
