934472-10-3Relevant academic research and scientific papers
Synthesis of N-tosylhomosphinganine and N-tosylsedridine
Chang, Meng-Yang,Lin, Chun-Yu,Wu, Tsun-Cheng,Sun, Pei-Pei
, p. 421 - 430 (2008/12/22)
A straightforward synthesis of N-tosylhomosphinganine and N-tosylsedridine has been achieved from trans-4-hydroxyproline by Grignard addition, regioselective Baeyer-Villiger reaction, cross or ring-closing metathesis and hydrogenation as the key steps.
An efficient approach to 2-substituted N-tosylpiperdines: asymmetric synthesis of 2-(2-hydroxy substituted)piperidine alkaloids
Bisai, Alakesh,Singh, Vinod K.
, p. 1907 - 1910 (2007/10/03)
We have developed an efficient and a general approach to chiral 2-substituted N-tosylpiperidines starting from chiral α-substituted-N-tosylaziridines. Using this approach, we have synthesized (+)-coniine. The synthesis of chiral N-tosyl-2-piperidinylethanol 15 and ent-15, was achieved from l- and d-aspartic acids, respectively in few steps. Piperidine 15 was converted into 2-(2-hydroxysubstituted)piperidines of type 2 in optically active form. By applying this strategy, asymmetric syntheses of halosaline (R,R)-2a, (+)- and (-)-sedamine 2b, (+)- and (-)-allosedamine 2c, (+)- and (-)-sedridine 2d, (+)- and (-)-allosedridine 2e, (+)-tetraponerine T-3 3a, T-4 3c, T-7 3b, and T-8 3d have been achieved in high yields. These stereoisomers can be interconverted via Mitsunobu inversion in excellent yields.
