- Reaction of bromomethylazoles and tosylmethyl isocyanide. A novel heterocyclization method for the synthesis of the core of marine alkaloids variolins and related azolopyrimidines
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A novel and efficient synthesis of the pyrido[3′,2′:4,5] pyrrolo[1,2-c]pyrimidine system, the heterocyclic core of the variolin family of marine alkaloids, is described. The route involves the reaction of 3-bromo-2-(bromomethyl)pyrrolo[2,3-b]pyridine and tosylmethyl isocyanide (TosMIC) under phase-transfer conditions. This unprecedented reaction was also used to synthesize a series of new methoxycarbonyl azolopyrimidines by reaction of TosMIC with bromomethylindoles, bromomethylbenzimidazole, and bromomethylpyrazole. Hydrolysis and decarboxylation of 5-bromo-7- methoxycarbonylpyrido[3′,2′:4,5]pyrrolo[1,2-c]pyrimidine obtained by this heterocyclization process and installation of the pyrimidine moiety in the C5 position open an alternative approach to complete a total synthesis of variolin B.
- Mendiola, Javier,Baeza, Alejandro,Alvarez-Builla, Julio,Vaquero, Juan J.
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p. 4974 - 4983
(2007/10/03)
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- Method for stimulating bone formation
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A method for stimulating bone formation by administering integrin binding compounds which cause the release of osteocalcin from osteoblasts is disclosed.
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- Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity
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Vitronectin receptor antagonists having the formula: STR1 which are useful for the treatment of inflammation, cancer and cardiovascular disorders, such as atherosclerosis and restenosis, and diseases wherein bone resorption is a factor, such as osteoporsis.
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