Cymaronic lactone

Cyclopentanophenanthrene, perhydro-3-hydroxy-, glycosides, I, 147 Cymarin, I, 148, 166 Cymaronic acid, phenylhydrazide and S-benzylthiuronium salt, I, 168 Cymaronic lactone, I, 165 Cymaronic lactone (1,4), 5-methyl-, I, 165... 

This conclusion was strengthened by the preparation of two different fully methylated cymaronic lactones. Cymarose was oxidized to cymaronic lactone, which was then methylated to give 5-methyl-cy-maronic lactone (1,4) (XLII), a sirup which was characterized by the phenylhydrazide of the corresponding acid. On the other hand, methyl cymaropyranoside was completely methylated to methyl 4-methyl-cymaropyranoside. The latter, after hydrolysis of the glycosidic methyl group and oxidation, yielded 4-methylcymaronic lactone (1,5) (XLIII), also a sirup, but which differed in rotation from the 1,4-lactone and formed a different phenylhydrazide. Further, the assignment of a 1,5 structure to XLIII was supported by the formation of a dimethoxy-glutaric acid on oxidation of XLIII with nitric acid. 

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