Destruxin analogues: Depsi peptidic bond replacement by amide bond
In order to determine the importance of the depsi bond present in natural destruxins, we have investigated the replacement of this ester bond by an amide bond, leading to a new family of analogues. Synthesis of six specific members of this new class of compounds is reported. Since none of these cyclopeptides showed any biological activity, we undoubtedly proved that the depside group is a requisite for insecticide effect.
Cavelier,Jacquier,Mercadier,Verducci
p. 6173 - 6186
(2007/10/03)
Asymmetric synthesis of N-methyl-α-amino esters from a glyoxal derived chiral heterocycle
The reaction between a chiral template derived from glyoxal with organometallic reagents leads ultimately to the optically active title compounds. The stereochemical outcome of the key-step which involves substitution of a thiophenol group depends on the organometallic: predominantly inversion with alkyl copper or complete retention with alkyl zinc halides. The stereodirecting effect of an allylic hydroxy group in an iminium intermediate is evidenced in the case of the organozinc reagent.
Agami,Couty,Prince,Puchot
p. 4343 - 4354
(2007/10/02)
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