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

Géant PierreYves | Zendy; Martínez Jean | Zendy; SalomRoig Xavier J. | Zendy

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

Author(s) -

Géant PierreYves,

Martínez Jean,

SalomRoig Xavier J.

Publication year - 2012

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201101333

Subject(s) - epoxide , chemistry , intramolecular force , hydrazone , reductive amination , stereochemistry , amination , ring (chemistry) , hydrolysis , lithium (medication) , nucleophile , alkaloid , medicinal chemistry , organic chemistry , catalysis , medicine , endocrinology

A general strategy leading to the synthesis of two cis ‐2‐methyl‐6‐substituted piperidin‐3‐ols is described. syn ‐(2 R ,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.

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