442682-29-3

Upstream product

• 83825-04-1 L-phenylalanine-L-proline methyl ester 
• 442682-28-2 2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carboxylic acid 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 347191-35-9 methyl 2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}-thiazole-4-carboxylate 

Downstream Products

• 442682-31-7 methyl (2S,3S)-2-[(2S,3S)-{(S)-1-[(S)-2-(2-{(S)-1-[(S)-2-tert-butoxycarbonylamino-3-phenylpropanoyl]pyrrolidin-2-yl}thiazol-4-ylcarbonylamino)-3-phenylpropanoyl]pyrrolidin-2-ylcarbonylamino}-3-methylpentanoylamino]-3-hydroxybutanoate 
• 442899-46-9 C₄₁H₄₉N₇O₆S 
• 259794-28-0 cis,cis-Ceratospongamide 
• 442682-30-6 (S)-1-[(S)-2-({2-[(S)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-pyrrolidin-2-yl]-thiazole-4-carbonyl}-amino)-3-phenyl-propionyl]-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

Synthetic studies on ceratospongamides, cyclic heptapeptides containing thiazole and oxazoline units: Total synthesis of cis, cis-ceratospongamide

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.