Premium
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.