Highly stereoselective construction of trans(2,3)- cis(2,6)-trisubstituted piperidines: An application to the chiral synthesis of Dendrobates alkaloids

• Published in: Tetrahedron Vol. 53; no. 28; pp. 9553 - 9574
• Main Authors: Toyooka, Naoki, Tanaka, Keiko, Momose, Takefumi, Daly, John W, Garraffo, H.Martin
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 14-07-1997
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(97)00641-8

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 Cl-epimer of quinolizidine 207I have been achieved.
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