JV-methyllaurotetanine

In 1964, isoboldine, as alkaloid A, methanolate (mp 121°-126°), solvent-free base (mp 180° [a] -p 41.2° in ethanol), was also reported in Symplocos celastrinea Mart., where it was found in large enough quantities that a variety of chemical transformations could be attempted (11). Treatment of either isoboldine (XXVIII) or the well-known boldine (XXX) with dihydropyran, then with diazomethane, and finally acid hydrolysis of the protective dihydropyranyl grouping, resulted in the formation of JV-methyllaurotetanine (XXIX), whose structiu-e had previously been clearly established. The hydroxyl group is therefore more reactive when at C-9 than when situated either at C-1 or C-2 (21). 

Several known aporphines have also been isolated from plants of the family Lauraceae, and these have been identified as actinodaphnine (27) [from the bark of Litsea gardneri (Thw.) Hook, f.] (41), isoboldine (28) [from the stem bark of Neolitsea fuscata (Thw.) Alston] (42), laurolitsine (29) [from the bark of Litsea gardneri (Thw.) Hook, f.] (41), and lauroteta-nine (30) and JV-methyllaurotetanine (31) [from the leaves of Actinodaphne speciosa Nees] (41). 

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