Biomimetic assemblies

Acetylene-based functionalized dihydrofuranones and related biomimetic assemblies 99H(51)2485. 

Figure 4.23 Synthesis space diagram for a ternary system composed of tetraethylorthosilicate (TEOS), cetyltrimethylammonium bromide (CTAB), and sodium hydroxide (H, hexagonal phase [MCM-41] C, cubic phase [MCM-48] L, lamellar phase [MCM-50] H20/Si02 = 100, reaction temperature 100°C, reaction time 10 days). (Reprinted from Science, Vol. 267, A. Firouzi, D. Kumar, L.M. Bull, T. Besier, R Sieger, Q. Huo, S.A. Walker, J.A. Zasadzinski, C. Glinka, J. Nicol, D.l. Margolese, G.D. Stucky, B.F. Chmelka, Cooperative Organization of Inorganic-Surfactant and Biomimetic Assemblies, pp. 1138-1143. Copyright 1995. With permission of AAAS.)...

C. Glinka, J. Nicol, D. Margolese, G.D. Stucky, and B.F. Chmelka, Cooperative Organization of Inorganic-Surfactant and Biomimetic Assemblies. Science, 1995, 267, 1138-1143. 

Firouzi, A. et al., Cooperative organization of inorganic-surfactant biomimetic assemblies, Science, 267, 1138, 1995. 

Leucoridine A (146) was synthesized by a biomimetic assembly of monomeric indole alkaloids (Scheme 6)." Geissoschizohne (152) was oxidized with Mn02 to give an indolenine, which was then treated with a catalytic amount of TEA to afford 19,20-dihydrovalparicine (153). This compound was further treated with a catalytic amount of TFA to afford leucoridine A (146). The mechanism for the formation of the central 3-spiro-l,2,3,4-tetrahydropyridine moiety was proposed, as shown in Scheme 6. 

Berggren G, Adamska A, Lambertz C, Simmons TR, Esselbom J, Atta M, Gambarelli S, Mouesca JM, Reijerse E, Lubitz W, Happe T, Artero V, Fontecave M (2013) Biomimetic assembly and activation of [FeFe]-hydrogenases. Nature 499(7456) 66-69. doi 10.1038/ nature12239... 

Nicol, J., Margolese, D., Stucky, G.D., and Chmelka, B.F. (1995) Cooperative organization of inorganic-surfectant and biomimetic assemblies. Science,... 

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