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Zur Kenntnis der Erythrophleum ‐Alkaloide. 18. Mitteilung. Die Struktur des Cassamins und des Erythrophlamins

1961; Wiley; Volume: 44; Issue: 6 Linguagem: Inglês

10.1002/hlca.19610440623

1522-2675

V. P. ARYA, Benjamin Engel,

Carbohydrate Chemistry and Synthesis

Cassamine and erythrophlamine are shown to contain a strongly hindered carbomethoxy group. The conversion of cassamine into 7β‐hydroxycassan‐19‐oic acid, that of erythrophlamine into 3β,7β‐dihydroxycassan‐l9‐oic acid, and the partial reduction of the dihydrodioxo monomethylester XIVa derived from erythrophlamine to dihydrocassamic acid IVa are described. These results, together with the proof of the position of the hindered carbomethoxy group in cassamine at C‐4, provided by D. W. MATHIESON et al. (cf.8)), establish structure IIa for cassamine and XIIa for erythrophlamine.