Tetrahedron

Total synthesis and conformational studies of ceratospongamide, a bioactive cyclic heptapeptide from marine origin

F Yokokawa, H Sameshima, Y In, K Minoura, T Ishida…

Index: Yokokawa, Fumiaki; Sameshima, Hirofumi; In, Yasuko; Minoura, Katsuhiko; Ishida, Toshimasa; Shioiri, Takayuki Tetrahedron, 2002 , vol. 58, # 40 p. 8127 - 8143

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Citation Number: 39

Abstract

The first total synthesis of cis, cis-ceratospongamide (cyclo [l-Pro-l-Ile-Me-oxazoline-l-Phe-l- Pro-thiazole-l-Phe-]) was accomplished and confirmed by X-ray crystal analysis. The heating of cis, cis-ceratospongamide in DMSO converted it not to the trans, trans isomer but to the trans, trans-[d-allo-Ile]-ceratospongamide, which was confirmed by total synthesis. Its solution conformation was constructed by the dynamic simulated annealing method using ...