Bastadins total synthesis

Kotoku N, Tsujita H, Hiramatsu A, Mori C, Koizumi N, Kobayashi M (2005) Efficient Total Synthesis of Bastadin 6, an Anti-Angiogenic Brominated Tyrosine-Derived Metabolite from Marine Sponge. Tetrahedron 61 7211... 

Scheme 9.12 Kobayashi and coworkers total synthesis of bastadin 6 [144],...

An efficient method for the conversion of iV>alkyl-lactams into the corresponding thiolactams, involving treatment with R3O+BF4- followed by NaSH, is reported. Twenty-four-membered macrocyclic amides containing phenylalanine and leucine units have been obtained. A total synthesis of the natural product bastadin-6, which has a 28-membered lactam ring, has been described, and total syntheses of ( )-maysine and ( >ma5dansinol are reported. ... 

Nishiyama, S, and Yamamura, S, (1982) Total synthesis of bastadins. Tetrahedron Lett., 23, 1281-1284. 

Kotoku, N., Tsujita, H., Hiramatsu, A., Mori, C Koizumi, N and Kobayashi, M. (2005) Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge. Tetrahedron, 61, 7211—7218. 

The diverse and unique chemical structures, and the variety of biological activities of bromotyrosine derivatives, make them ideal synthetic targets for synthetic and natural products chemists. Studies on the synthesis of bromotyrosine can be traced back to 1912 (194). In former studies, degradation, chemical transformation to known compoimds, or even total synthesis were conducted for the purpose of verifying the structures. Later studies were focused on the total synthesis of more complex structures, such as the spirocyclohexadienylisoxazoline and bastadin ring systems. 

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