442899-46-9Relevant articles and documents
Synthetic studies on ceratospongamides, cyclic heptapeptides containing thiazole and oxazoline units: Total synthesis of cis, cis-ceratospongamide
Kutsumura, Noriki,Sata, Noriko U.,Nishiyama, Shigeru
, p. 847 - 850 (2007/10/03)
A total synthesis of cis, cis-ceratospongamide 1a, a cycloheptapeptide isolated from the Indonesian red alga Ceratodictyon spongiosum and the symbiotic sponge Sigmadocia symbiotica, was accomplished. The heptapeptide chain 8 was produced by a stepwise connection of the following segments: (L-Phe-L-Pro)-thiazole residue, L-Phe-L-Pro-OMe, and L-Ile-L-aThr-OMe. Macrolactamization of 8, followed by cyclization to an oxazoline ring, provided cis, cis-ceratospongamide 1a along with its diastereomer 1c, which was different from the reported trans, trans-ceratospongamide 1b. The structural determination of 1c and its conversion to 1a were successfully achieved.