Collect. Czech. Chem. Commun. 1992, 57, 1459-1465

Absolute Stereochemistry of (-)-Wieland-Miescher Ketone as Established by the X-ray Crystallographic and CD Exciton Chirality Methods

Nobuyuki Haradaa, Tatsuo Sugiokaa,b, Hisashi Udaa and Takeo Kurikib

a Institute for Chemical Reaction Science, Tohoku University, 2-1-1 Katahira, Aoba, Sendai 980, Japan
b Pharma Research Laboratory, Hoechst Japan Ltd., 1-3-2 Minamidai, Kawagoe, Saitama 350, Japan


The 8aR absolute stereochemistry of Wieland-Miescher ketone (-)-I was established by the X-ray structure analysis of its bis(4-bromobenzoate) derivatives (1R,6R,8aR)-(+)-IV and (1R,6S,8aR)-(-)-V. The absolute configuration of (-)-I was corroborated further by the application of the CD exciton chirality method to bis(4-bromobenzoates) (+)-IV and (-)-V.