TY - JOUR
T1 - Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions
T2 - Application to the total synthesis of (±)-epi-indolizidine 167B and 209D
AU - Saikia, Anil K.
AU - Indukuri, Kiran
AU - Das, Jagadish
PY - 2014/9/28
Y1 - 2014/9/28
N2 - A diastereoselective protocol has been established for the synthesis of 4-O-tosyl piperidine containing hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol- 6(2H)-one derivatives via the aza-Prins cyclization reaction of cyclic N-acyliminium ions mediated by p-toluene sulphonic acid (p-TSA) under mild conditions. The reaction is highly diastereoselective and gives excellent yields. This method has been applied to an efficient total synthesis of indolizidine alkaloids, (±)-epi-indolizidine 167B and 209D. This journal is
AB - A diastereoselective protocol has been established for the synthesis of 4-O-tosyl piperidine containing hexahydroindolizin-3(2H)-one, hexahydro-1H-quinolizin-4(6H)-one and 1,3,4,10b-tetrahydropyrido[2,1-a]isoindol- 6(2H)-one derivatives via the aza-Prins cyclization reaction of cyclic N-acyliminium ions mediated by p-toluene sulphonic acid (p-TSA) under mild conditions. The reaction is highly diastereoselective and gives excellent yields. This method has been applied to an efficient total synthesis of indolizidine alkaloids, (±)-epi-indolizidine 167B and 209D. This journal is
UR - http://www.scopus.com/inward/record.url?scp=84906534122&partnerID=8YFLogxK
U2 - 10.1039/c4ob01130a
DO - 10.1039/c4ob01130a
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C2 - 25072604
AN - SCOPUS:84906534122
SN - 1477-0520
VL - 12
SP - 7026
EP - 7035
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 36
ER -