Advance Biofactures Corporation

Thomas Y Tsai

Karel Wiesner

Connie S Tsai

Rinaldo Marini-Bettolo

This invention relates to novel isomers of naturally occurring cardiotonic compounds, specifically novel isobufalins and novel isoresibufogenins. This invention also relates to a novel method of preparing the novel isomers.

Novel isomers of bufalin and resibufogenin and their preparation

A method for synthesizing a cardenolide or isocardenolide by subjecting an .alpha.,.beta.-unsaturated steroidal 17-ketone to a double bond shift and hydrogenation to produce a (C/D cisoid) ketone which is treated with an organometallic reagent to yield a tertiary alcohol and the acidifying said alcohol to produce said cardenolide or isocardenolide is shown. The invention also relates to organometallic reagents particularly useful in such method.

Organometallic reagents and their use in the synthesis of cardenolides

The invention relates to furyl intermediates and the preparation thereof, said intermediates being particularly useful in the preparation of synthetic cardenolides and their isomers. The process provides for the reaction of an unsaturated steroidal 17 ketone with a .beta.-furyl compound to produce an allylic alcohol which is subjected to acetylation and allylic rearrangement. The resulting material is then hydrogenated to produce the furyl intermediate. Cardenolides are formed therefrom by oxidation of the furyl intermediates.

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Fredericton, Canada

Thomas Y Tsai