Fumiquinazoline alkaloids

Figure 15.2 Solid-phase synthesis of fumiquinazoline alkaloids by Wang and Ganesan [11],...

Wang and Ganesan [92], in the process of synthesizing a series of fumiquinazoline alkaloids, reported the extensive use of long-range H- i N... 

Wang, H., Ganesan, A. Total Synthesis of the Fumiquinazoline Alkaloids Solution-Phase Studies. J. Org. Chem. 2000, 65,1022-1030. 

SCHEME 35. Solid-phase synthesis of fumiquinazoline alkaloids. 

Wang H, Ganesan A. Total synthesis of the fumiquinazoline alkaloids solid-phase studies. J. Comb. Chem. 2000 2 186-194. 

Several groups of quinazoline alkaloids involving pyrazino[2,l-fo]quinazoline-3,6-dione substructure are found in fungal metabolites. These include glyantrypine (21) [87], fumiquinazolines A-E, F (22), G (23) [88,89], H and I [90], and fiscalines A-C [91,92]. Novel spiro-type pyrazinoquina-... 

Ames BD, Liu X, Walsh CT (2010) Enzymatic processing of fumiquinazoline F a tandem oxidative-acylation strategy for the generation of multicyclic scaffolds in fungal indole alkaloid biosynthesis. Biochemistry 49 8564—8576... 

For example, in 2000, Wang and Ganesan constructed the fumiquinazoline F alkaloids on solid phase (Scheme 3.5). " Initially, Fmoc-L-Trp was loaded onto Wang resin to give 7. Using the chiral amino acid at this stage actually installed the key stereocenter of alkaloid 11. 

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