81149-89-5Relevant academic research and scientific papers
Synthetic Studies on Electron Transport Inhibitors. Part 2. Approaches to the Synthesis of Myxalamide D
Cox, Catherine M.,Whitting, Donald A.
, p. 1907 - 1911 (2007/10/02)
In a synthetic approach to ethyl myxalate-D 5 (X=OEt) the butendial monoacetals 12 and 15 were transformed by a Wadsworth-Emmons reaction and controlled hydrolysis into the (E,E)-aldehydoester (17); a Z-selective reaction with Bestmann's ylide 18 afforded
Cumulated Ylides, XII. A Stereoselective Synthetic Method for (Z)-α,β-Unsaturated Aldehydes
Bestmann, Hans Juergen,Roth, Kurt,Ettlinger, Manfred
, p. 161 - 171 (2007/10/02)
(2-Ethoxyvinyl)triphenylphosphonium bromide (5) is converted with sodium amide into the corresponding phosphaallenylide 6 which adds ethanol forming the ylide 7. 7 is also obtained by the reaction of 5 with sodium ethanolate.The Wittig reaction of 7 with aldehydes 2 proceeds with high (Z)-stereoselectivity to give (Z)-α,β-unsaturated acetals 8 which are cleaved under well defined conditions with p-toluenesulfonic acid or with wet silica gel to (Z)-α,β-unsaturated aldehydes 9.
