862463-98-7Relevant academic research and scientific papers
Total synthesis of enantiopure β-D-mannosyl phosphomycoketides from Mycobacterium tuberculosis
Van Summeren, Ruben P.,Moody, D. Branch,Feringa, Ben L.,Minnaard, Adriaan J.
, p. 4546 - 4547 (2007/10/03)
The first stereoselective total synthesis of a β-d-mannosyl phosphomycoketide is reported. To introduce the stereogenic centers in the chain, three linear chiral building blocks were prepared using two different asymmetric catalytic conjugate addition protocols. Coupling of the various linear fragments was affected using a Julia-Kocienski sequence. This approach constitutes a general and convergent method for the construction of saturated oligoisoprenoid chains of any length and stereochemistry. In addition, an alternative approach for the formation of the difficult β-mannosyl phosphate linkage was shown to be successful. Biological evalutation of the all-S compound revealed that its antigenic potency for T cells is identical to that of the natural product. This result implies that the fine structure of the lipid part has a strong influence on biological activity and that the T cell response is discriminating between different stereoisomers. Copyright
An iterative catalytic route to enantiopure deoxypropionate subunits: Asymmetric conjugate addition of Grignard reagents to α,β-unsaturated thioesters
Des Mazery, Renaud,Pullez, Maddalena,Lopez, Fernando,Harutyunyan, Syuzanna R.,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 9966 - 9967 (2007/10/03)
A highly enantioselective (up to 96% ee) conjugate addition of Grignard reagents, in particular, MeMgBr, to α,β-unsaturated thioesters is provided as well as its application to a diastereo- and enantioselective iterative route to syn- and anti-1,3-dimethyl arrays and deoxypropionate subunits. The versatility of the method is illustrated in the synthesis of (-)-lardolure, a multimethyl-branched insect natural pheromone. Copyright
