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New Studies and a Reinvestigation on [4+2] Cycloadditions of (−)‐Thebaine: Asymmetrical Diels‐Alder Reactions with a Conformationally Fixed Chiral Diene
Author(s) -
Pindur Ulf,
Keilhofer Diana
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301151
Subject(s) - thebaine , chemistry , diene , cycloaddition , diels–alder reaction , selectivity , alkaloid , stereochemistry , medicinal chemistry , organic chemistry , catalysis , medicine , natural rubber , codeine , morphine , pharmacology
Some novel Diels‐Alder reactions of the opium alkaloid (−)‐thebaine ( 1 ) as an electron‐rich diene and a reinvestigation of its reactions with cyclic and acyclic dienophiles are described. The π‐facial selectivity has been studied on the basis of structural analyses of the cycloadducts. Some related results on [4 + 2] cycloaddition reactions of 1‐methoxy‐1,3‐cyclohexadiene ( 11 ) are also reported.