Jaspamide synthesis

Synthesis, Conformational Analysis, and Cytotoxicity of New Analogues of the Natural Cyclodepsipeptide Jaspamide. J Nat Prod 67 1325... 

Synthesis, Solution Structure, and Bioactivity of Six New Simplified Analogues of the Natural Cyclodepsipeptide Jaspamide. Bioorg Med Chem 13 5225... 

Geodiamolide A (203) and jaspamide (204) are cytotoxic antifungal cyclic depsipeptides of marine sponge origin. The key component 207 required for their synthesis is achieved via coupling of acid 206 with amine 205 using DEPC.77... 

Kato, S., Hamada, Y., and Shioiri, T. (1988) A practical synthesis of the peptide part of jaspamide (jasplakinolide), a cydodepsipeptide from a marine sponge. Tetrahedron Lett., 29, 6465-6466. 

Schmidt, U., Siegel, W., and Mundinger, K. (1988) Total syntheses of jaspamide (jasplakinolide) and geodiamolide A and B —1. Stereoselective synthesis of (2S,4E,6R,8E)-8-hydroxy-2,4,6-trimethyl-4-nonenoic. Tetrahedron Lett., 29,1269-1270. 

Hirai, Y, Yokota, K., and Momose, T. (1994) Studies on the novel cyclodepsipeptides. A total synthesis of (+)-jasplakinolide (jaspamide). Heterocycles, 39, 603-612. 

Ashworth, P., Broadbelt, B., Jankowski, P., Kodenski, P., Pimm, A., and Bell, R. (1995) A synthesis of jaspamide based on 1,2-metallate rearrangements of a-heteroalkenylmetal derivatives. Synthesis, 199-206. 

Zhang, P., Liu, R., and Cook, J.M. (1995) A condse synthesis of optically active 2-bromo-tryptophan amino adds present in konbamide and jaspamide via a regiospedfic bromination procedure. Tetrahedron Lett., 36, 9133-9136. 

Celanire, S., Descamps-Erancois, C., Lesur, B., Guillaumet, G., and Joseph, B. (2005) Synthesis of 14-membered ring jaspamide derivatives. Lett. Org. Chem., 2, 528-531. 

Terracciano, S., Bruno, L, Bifulco, G., Avallone, E., Smith, C.D., Gomez-Paloma, L., and Riccio, R. (2005) Synthesis, solution structure, and bioactivity of six new simplified analogues of the natural cydodepsipeptide jaspamide. Bioorg. Med. Chem., 13, 5225-5239. 

The total synthesis of polycitone A (280) and B (281) (243), and the cyclodepsi-peptides, jaspamide (259) (244), geodiamolide A (260) (245), and geodiamolide B (261) (246) were also reported. Since these are not typical bromotyrosine derivatives, the details of the syntheses are not included here. 

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