350237-01-3Relevant academic research and scientific papers
Synthesis of taurospongin A
Wu, Boshen,Mallinger, Aurelie,Robertson, Jeremy
supporting information; experimental part, p. 2818 - 2821 (2010/09/03)
(Figure presented) Two new routes to the C(1-10) carboxylic acid core of taurospongin A are presented. In the first route, overall asymmetric hydration of a C(2)-C(3) alkene is achieved by Sharpless AD and selective deoxygenation at C(2); in the second route, the C(3) stereogenic center is set by Tietze asymmetric allylation. A short synthesis of the C(1′-25′) fatty acid combines with the product from the first route to complete the total synthesis of taurospongin A.
A diastereoselective intramolecular hydroamination approach to the syntheses of (+)-, (±)-, and (-)-pinidinol
Molander,Dowdy,Pack
, p. 4344 - 4347 (2007/10/03)
A diastereoselective, lanthanocene-catalyzed, intramolecular hydroamination reaction was applied to the preparation of 2,6-disubstituted piperidines. Various metal/ligand arrays in the catalysts were examined using a model substrate to allow optimization of the diastereoselectivity. It was determined that the relationship between metal size and ligand bulk plays an integral role in the transformation. The complex Cp*2NdCH(TMS)2 converted 2-substituted 8-nonen-4-amines to 2,6-disubsituted piperidines with greater than 100: 1 selectivity for the formation of the cis isomer. A short synthesis of pinidinol, an alkaloid isolated from various pine and spruce species, was then carried out to exploit this stereoselective reaction.
