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Communication | Regular issue | Vol 3, No. 6, 1975, pp.467-470
Published online, 1st January, 1970
DOI: 10.3987/R-1975-06-0467
Synthesis of Optically Active Ochotensanes

Jiro Imai, Yoshikazu Kondo,* and Tsunematsu Takemoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Treatment of l-(14S)-β- (Ia) and d-(14R)-β-canadine methochlorides (Ib) with organolithiums, lithium aluminium hydride, or sodium methylsulfinyl carbanion in tetrahydrofuran gave d- (IIa) and l-2,3-methylenedioxy-9,10-dimethoxyochotensanes (IIb), respectively. The structures of those have been proved by the results of the Hofmann degradation and spectral means. The cd spectra of IIa and IIb showed Davydov split extrema centered at 284 nm whose first Cotton effects corresponded to the absolute configurations.