Copper-catalyzed cross-coupling of amino acid-derived amides with (Z)-vinyl iodides: Unexpected solvent effect and preparation of plocabulin
A copper-catalyzed cross-coupling reaction of amino acid-derived amides and (Z)-vinyl iodide was studied to improve a key step in the synthesis of plocabulin, a novel microtubule destabilizer agent of marine origin. The study revealed a profound solvent effect with 1,2-dimethoxyethane (DME), which gave consistently high yields across a large variety of the amide and (Z)-vinyl iodide substrates. The protocol was successfully utilized in the preparation of plocabulin and provided a significantly improved yield.
A multicomponent coupling strategy suitable for the synthesis of the triene component of the oxazolomycin antibiotics.
Concise and versatile routes suitable for the synthesis of three geometric isomers of an analogue of the left hand triene sub-unit of oxazolomycin are reported. A strategy based upon a key Heck reaction was unsuccessful, and this was traced to a combinati
Bulger, Paul G,Moloney, Mark G,Trippier, Paul C
p. 3726 - 3737
(2007/10/03)
A new Procedure for the Synthesis of (E)-1-iodo-1-alkenes
(E)-1-iodo-1-alkenes 4 can be prepared stereoselectively from aldehydes 1 via IH-elimination of 1,1-di-iodoalkanes 3 with DBU. Key words: Vinyl iodide; diiodoalkane; elimination; stereoselectivity.
Martinez, A. Garcia,Alvarez, R. Martinez,Gonzalez, S. Martinez,Subramanian, L. R.,Conrad, M.
p. 2043 - 2044
(2007/10/02)
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