TY - JOUR
T1 - Highly stereoselective construction of trans(2,3)-cis(2,6)- Trisubstituted piperidines
T2 - An application to the chiral synthesis of dendrobates alkaloids
AU - Toyooka, Naoki
AU - Tanaka, Keiko
AU - Momose, Takefumi
AU - Daly, John W.
AU - Garraffo, H. Martin
N1 - Funding Information:
We are grateful to Professor C. Kibayashi, Tokyo University of Pharmacy & Life Science, for kindly providing us with 1H and 13C NMR spectra of (-)-12. We acknowledge partial financial support from the Ministry of Education, Sciences and Culture, the Japanese Government \[ScientificR esearch (# 06772065)\].
PY - 1997/7/14
Y1 - 1997/7/14
N2 - A general and flexible route to the 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine system found in Dendrobates alkaloids has been developed. The key step for this synthesis is the highly stereoselective Michael reaction of a didehydropiperidinecarboxylate (1) to afford a trans(2,3)-cis(2,6)-trisubstituted piperidine. In this manner, the chiral formal synthesis of indolizidines 207A and 209B and the total synthesis of indolizidines 223J, 235B and C1-epimer of quinolizidine 207I have been achieved.
AB - A general and flexible route to the 5,8-disubstituted indolizidine and 1,4-disubstituted quinolizidine system found in Dendrobates alkaloids has been developed. The key step for this synthesis is the highly stereoselective Michael reaction of a didehydropiperidinecarboxylate (1) to afford a trans(2,3)-cis(2,6)-trisubstituted piperidine. In this manner, the chiral formal synthesis of indolizidines 207A and 209B and the total synthesis of indolizidines 223J, 235B and C1-epimer of quinolizidine 207I have been achieved.
UR - http://www.scopus.com/inward/record.url?scp=0030788403&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(97)00641-8
DO - 10.1016/S0040-4020(97)00641-8
M3 - 学術論文
AN - SCOPUS:0030788403
SN - 0040-4020
VL - 53
SP - 9553
EP - 9574
JO - Tetrahedron
JF - Tetrahedron
IS - 28
ER -