Geodiamolide synthesis

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... 

Grieco, P.A. and Perez-Medrano, A. (1988) Total synthesis of the mixed peptide-polypropionate based cyclodepsipeptide (+)-geodiamolide B. Tetrahedron Lett., 29, 4225-4228. 

Shioiri, T, Imaeda, T, and Hamada, Y. (1997) An expeditious synthesis of geodiamolide A, an 18-membered cytotoxic depsipeptide from marine sponges. Heterocycles, 46, 421-442. 

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. 

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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