Benzyltetrahydroisoquinoline Alkaloids with Four Oxygenated Substituents

Benzyltetrahydroisoquinoline Alkaloids with Four Oxygenated Substituents 

On the basis of the above data structure XLVII has been assigned to thalifendlerine the possibility of having the isomeric structure L was discarded by synthesis of the latter compound through the Bischler-Napieralski route. It was different (mp 122°) from the natural base. 

Methylation of XLVII with diazomethane gave 0-methylthali-fendlerine (mp 195°-197°) which proved to be identical with tetra-hydrotakatonine (Section IV, A). 

L-( + )-ReticuIine, C19H23NO4 (LI), was first isolated from Annona reticulata Linn. (Annonaceae) by Gopinath et al. (9S). It has also been found in Cinnamomum camphora (Linn.) Sieb. (Lauraceae) (99), in hylica rogersii Pillans (Rhamnaceae) (100), in opium (101), and in Thailand Joss pow der, a product presumably reduced from plants of the Machilus genus (65). Racemic reticuline has been isolated from opium and from the mother liquors of the purification of morphine (102). 

The type of substitution and the configuration of (+ )-reticuline were determined by Gopinath et al. (98) by transformation into l-( + )-laudanosine (XXXVII R = CH3) on treatment with diazomethane. The position of the phenolic hj droxyl groups was established by ethylation and oxidation of the (-t )-di-0-ethylreticuline (LII). 3-Ethoxy-4-methoxybenzoic acid (LIII) and 3-ethoxy-4-methoxyphtalic acid (LIV) 

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III. Benzyltetrahydroisoquinoline Alkaloids with Four Oxygenated Substituents 418... 

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