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2004
Alkaloids
U 0600
46- 201
The First Example of the Stereoselective Synthesis of 7β-Carbamoyl-4,5α-epoxymorphinan via a Novel and Reactive γ-Lactone. — Title compounds (VII) are
stereoselectively synthesized from 7α-carboxylate (IV) and amines (V) in the presence
of DBU. Rationalization of this unexpected transformation involves the formation of
the novel and reactive lactone (VIII), which reacts with amines via ring opening to give
derivatives of type (VIIb), cf. (VIIIb)→(VIIb). The stereoselective synthesis of 7α-carbamoyl analogues, cf. (IX), is also carried out. — (FUJII, H.; HIRANO, N.; UCHIRO,
H.; KAWAMURA*, K.; NAGASE, H.; Chem. Pharm. Bull. 52 (2004) 6, 747-750;
Pharm. Res. Lab., Toray Ind., Inc., Kanagawa 248, Japan; Eng.) — M. Paetzel
2004
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