854027-91-1Relevant academic research and scientific papers
Synthesis of polyhydroxylated quinolizidine and indolizidine scaffolds from sugar-derived lactams via a one-pot reduction/Mannich/Michael sequence
Szczesniak, Piotr,Stecko, Sebastian,Maziarz, Elzbieta,Staszewska-Krajewska, Olga,Furman, Bartlomiej
, p. 10487 - 10503 (2014)
A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz's reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky's diene. The stereochemical course of the investigated reaction has been explained in detail. The obtained bicyclic products are attractive building blocks for the synthesis of various naturally occurring polyhydroxylated alkaloids and their derivatives.
Synthesis and biological evaluation of conformationally constrained analogues of the antitubercular agent ethambutol
Faugeroux, Vanessa,Genisson, Yves,Salma, Yahya,Constant, Patricia,Baltas, Michel
, p. 5866 - 5876 (2008/03/18)
Three (S)-prolinol-derived conformationally restricted analogues of the antitubercular agent ethambutol were prepared and tested against Mycobacterium tuberculosis.
Total synthesis of (+)-batzelladine A and (-)-batzelladine D via [4 + 2]-annulation of vinyl carbodiimides with N-alkyl imines
Arnold, Michael A.,Day, Kenneth A.,Duron, Sergio G.,Gin, David Y.
, p. 13255 - 13260 (2008/03/11)
A diastereoselective [4 + 2]-annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich polycyclic guanidine cores of the batzelladine alkaloids. Application of this strategy, together with additional key steps such as long-range directed hydrogenation and diastereoselective intramolecular iodo-amination, led to highly convergent total syntheses of (-)-batzelladine D and (+)-batzelladine A with excellent stereocontrol.
Diastereoselective [4+2] annulation of vinyl carbodiimides with N-alkyl imines. Asymmetric synthetic access to the batzelladine alkaloids
Arnold, Michael A.,Duron, Sergio G.,Gin, David Y.
, p. 6924 - 6925 (2007/10/03)
A diastereoselective [4+2] annulation of vinyl carbodiimides with chiral N-alkyl imines has been developed to access the stereochemically rich tricyclic core of the batzelladine alkaloids. Its application to the asymmetric synthesis of batzelladine D perm
