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Stereoselective Synthesis of Substituted Piperidines – Total Synthesis and Absolute Configurations of (+)‐ and (–)‐Dienomycin C
Author(s) -
Ripoche Isabelle,
Canet JeanLouis,
Gelas Jacques,
Troin Yves
Publication year - 1999
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/(sici)1099-0690(199907)1999:7<1517::aid-ejoc1517>3.0.co;2-h
Subject(s) - enantiopure drug , chemistry , diastereomer , total synthesis , stereoselectivity , absolute configuration , stereochemistry , absolute (philosophy) , alkaloid , enantioselective synthesis , organic chemistry , catalysis , philosophy , epistemology
The first total asymmetric synthesis and the attribution of the absolute configurations of (+)‐dienomycin C ( 1 ), an alkaloid isolated from a Streptomyces strain, are reported. This compound was prepared in six steps from the enantiopure tricarbonyl(dienal)iron complex (+)‐ 4 which is easily obtained by separating preformed diastereomers, starting from phenylpentadienoic acid and ( S )‐methyl mandelate.