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Enantioselective Synthesis of (−)‐Anaferine Dihydrochloride by a Ruthenium‐Catalysed Tandem Ring Rearrangement Metathesis
Author(s) -
Blechert Siegfried,
Stapper Christian
Publication year - 2002
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 - 10.1002/1099-0690(200208)2002:16<2855::aid-ejoc2855>3.0.co;2-1
Subject(s) - chemistry , enantioselective synthesis , metathesis , cycloheptene , tandem , ruthenium , total synthesis , stereochemistry , stereoselectivity , ring (chemistry) , derivative (finance) , yield (engineering) , catalysis , organic chemistry , materials science , composite material , polymerization , polymer , financial economics , economics , metallurgy
A stereoselective synthesis of (−)‐anaferine dihydrochloride has been developed. The bis(tetrahydropyridine) system 10 was formed by a tandem ring rearrangement metathesis of the chiral bis(but‐3‐enylamino)cycloheptene derivative 9 . (−)‐Anaferine dihydrochloride was obtained in 23% overall yield in eleven steps and its absolute configuration was confirmed as ( R , R ) by this total synthesis.