The configuration of cevine (cas 124-98-1)☆☆☆

Add time:09/08/2019    Source:sciencedirect.com

The alkaloid cevine has been shown to have configuration II. The configurations of nine (C3, C4, C5, C9, C10, C12, C14, C17, C25) of the fourteen asymmetric centers were established by earlier work. Hydrogenation of 16-dehydrocevine 3,4-diacetate (XIII) over platinum proceedeb stereoselectively to cevine 3,4-diacetate (XIV). Sodium borohydride reduction of 16-dehydrocevadine-D-orthoacetate-4-acetate (XVII) afforded a mixture of cevadine-D-orthoacetate 4-acetate (XVIII) and 16-epicevadine-D-orthoacetate 4-acetate (XVI). Both XVIII and XVI were submitted to alkaline hydrolysis followed by acid treatment to give cevagenine C-orthoacetate (XX) and 16-epicevagenine-C-orthoacetate (XIX). XIX consumed lead tetraacetate faster than XX, thereby indicating β-orientation for the C16 hydroxyl of cevine. Arguments are presented for assignment of configurations at C8, C13 and C20. Oxdiation of veracevine-D-orthoacetate triacetate (XXII) with N-bromosuccinimide gave a bridged oxide (XXIII) which, in turn, afforded a formamido ketone (XXIV) on chromic anhydride-pyridine oxidation. The bridged β-oriented oxide structure of XXIII requires that the hydrogen at C22 be α-oriented.

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