347191-27-9Relevant articles and documents
Kinetic control of proline amide rotamers: Total synthesis of trans,trans- and cis,cis-ceratospongamide
Deng, Shaojiang,Taunton, Jack
, p. 916 - 917 (2007/10/03)
Ceratospongamide is a cyclic peptide natural product that is biosynthesized as a mixture of two proline rotamers. Remarkably, these rotamers do not detectably interconvert at temperatures up to 100 °C. Here we report high-yielding syntheses of each rotame
Total synthesis of cis,cis-ceratospongamide, a bioactive thiazole-containing cyclic peptide from marine origin
Yokokawa,Sameshima,Shioiri
, p. 986 - 988 (2007/10/03)
The first total synthesis of cis,cis-ceratospongamide (1a), isolated from marine source, was accomplished via thiazole synthesis using CMD methodology, DEPC-mediated peptide coupling, macrolactamization, and cyclodehydration. Comparison of the cyclization sites and coupling reagents in the macrolactamization step was also investigated.