Crystal structure and relative configuration of (±)-11,12-dihydroglaziovine. Stereochemistry of reduced proaporphines

Abstract

The relative configuration of the two asymmetric centres of (±)-11,12-dihydroglaziovine(3)was established by the X-ray determination of the crystal and molecular structure of its hydrobromide[a= 14.607(1), b= 17.452(2), c= 13.591(1)Å, Z= 8, space group Pbca, orthorhombic, final R 0.036 for 1 343 reflections]. (±)-11,12-Dihydroglaziovine was found to be the 6aS* : 7aS* diastereoisomer. The conformations of the four atomic rings present inthe molecule are also discussed, and the stereochemistry deduced of related series of reduced proaporphines.