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A Route to "all-cis" 2-Methyl-6-Substituted Piperidin-3-ol Alkaloids from syn-(2R,1′S)-2-(1-Dibenzylaminomethyl)epoxide: Rapid Total Synthesis of (+)-Deoxocassine

A general strategy leading to the synthesis of two cis‐2‐methyl‐6‐substituted piperidin‐3‐ols is described. syn‐(2R,1′S)‐2‐(1‐Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza‐enolate of hydrazones 12...

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Bibliographic Details
Published in:European Journal of Organic Chemistry 2012-01, Vol.2012 (1), p.62-65
Main Authors: GEANT, Pierre-Yves, MARTINEZ, Jean, SALOM-ROIG, Xavier J
Format: Article
Language:English
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Summary:A general strategy leading to the synthesis of two cis‐2‐methyl‐6‐substituted piperidin‐3‐ols is described. syn‐(2R,1′S)‐2‐(1‐Dibenzylaminomethyl) epoxide (13) was used as common building block. The key step involved oxirane ring opening of 13 by the nucleophilic lithium aza‐enolate of hydrazones 12a and 12b. Subsequent hydrazone hydrolysis and intramolecular reductive amination afforded the alkaloid (+)‐deoxocassine and a new C‐6 ethyl analogue of this substance in good yields. The total synthesis of (+)‐deoxocassine and its new C‐6 ethyl analogue is reported. The key step of this synthetic pathway involves C–C coupling between syn‐(2R,1′S)‐2‐(1‐dibenzylaminomethyl)epoxide and an aza‐enolate of a hydrazone intermediate. This protocol is suitable to synthesize other “all‐cis” 2‐methyl‐6‐substituted piperidine‐3‐ol alkaloids.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201101333