Methyl aplysinopsin

Some new six-membered Aplysinopsin analogues, 5-(17f-indol-3-ylmethylene)-2,4,6(17f,3/7,5//)-pyrimidinetriones 678, were prepared in 11-73% yield from indole derivatives 676 and 5-[(dimethylamino)methylene]-2,4,6(l/7,3/7,5//)-pyrimidinetriones 677 by heating in glacial acetic acid (Equation 162) <2001T3159>. 2-Methylindole reacts with pyrimidinetrione 677b (when R = Me) in a different manner from 677a (when = H). Instead of the expected 3-vinylindole 678, 3-[bis(2-methyl-l//-indol-3-yl)methyl]-2-methyl-l//-indole 679 was isolated in 71% yield (Scheme 135). 

Examples of five-membered heterocyclic rings prepared by aza-Wittig and related methods include the alkaloid leucettamine B (206) and pyrrolo[2,3-b]pyridines (207) (Scheme20). The aza-Wittig reactions of the iminophosphorane (208) with methyl isocyanate, carbon dioxide, or carbon disulfide give heterocumulenes (209), (210), and (211), respectively, which react with amines or ammonia to provide a route to the framework of aplysinopsin alkaloids (212). ... 

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