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

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...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 28; pp. 9553 - 9574
Main Authors Toyooka, Naoki, Tanaka, Keiko, Momose, Takefumi, Daly, John W, Garraffo, H.Martin
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.07.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
209B
ASYMMETRIC-SYNTHESIS
PUMILIOTOXINS
INDOLIZIDINES
QUINOLIZIDINES
PYRROLIZIDINES
207A
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)00641-8