131618-41-2Relevant academic research and scientific papers
Enantioselective Total Synthesis of (+)- and (-)-Pyrrolidine 197B, a New Class of Alkaloid from the Dendrobatid Poison Frog: Assignment of the Absolute Configuration
Machinaga, Nobuo,Kibayashi, Chihiro
, p. 1386 - 1393 (2007/10/02)
Enantioselective total synthesis of both enantiomers of pyrrolidine 197B (1), a new class of dendrobatid alkaloid, is described.The synthesis begins with the C2 symmetric S,S or R,R diepoxides 4, derived from (S,S)-1,2,5,6-hexanetetraol (2) as a single common chiral synthon, and involves pyrrolidine formation via the cyclic sulfonates to afford (+)- or (-)-1, respectively.The (+) and (-) enantiomers of 1 were converted to the corresponding N-benzoyl derivatives (+)-27 and (-)-27, which were directly compared with 27 derived from natural 1 by HPLC using a Chiracel column.This comparison established the absolute stereochemistry of the natural enantiomer of pyrrolidine 197B as 2S,5S.
ENANTIODIVERGENT TOTAL SYNTHESIS OF NATURALLY OCCURING trans-2-BUTYL-5-PENTYLPYYROLIDINE
Machinaga, Nobuo,Kibayashi, Chihiro
, p. 3637 - 3640 (2007/10/02)
The enantiodivergent total synthesis of (+)-(2S,5S)- and (-)-(2R,5R)-trans-2-butyl-5-pentylpyrrolidines was effected from the C2 symmetric (S,S)- and (R,R)-diepoxides, respectively, both prepared from D-mannitol, by a sequence involving stereo-defined ring construction of the unsymmetrical trans-2,5-dialkylpyrrolidine via the cyclic sulfate as a key step.
