221677-52-7Relevant academic research and scientific papers
Study on fungitoxic 3-amino-2-piperidinone-containing lipids: Total syntheses of cepaciamides A and B
Toshima, Hiroaki,Maru, Kazuko,Saito, Masatoshi,Ichihara, Akitami
, p. 939 - 942 (2007/10/03)
Total syntheses of cepaciamides A and B were accomplished. In the preparation of two fatty acid segments, (S)-malic acid was used as a chiral source to introduce (2S)-configuration. A known chiral cyclopropane derivative was introduced in the segment of cepaciamide A. The formation of (Z)-olefin in the segment of cepaciamide B was achieved by means of partial reduction of the acetylenic bond. Estexification between fatty acid segments and amide segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides.
Total syntheses of cepaciamides A and B, novel fungitoxic 3-amino-2- piperidinone-containing lipids produced by Pseudomonas cepacia D-202
Toshima, Hiroaki,Maru, Kazuko,Saito, Masatoshi,Ichihara, Akitami
, p. 5793 - 5808 (2007/10/03)
Total syntheses of cepaciamides A and B were accomplished. (R)-3-Amino- 2-piperidinone was obtained via cyclization of (R)-ornithine. The common amide-linked fatty acid was synthesized via Sharpless AD as the key step. Amide-formation was achieved with DEPC. In the preparation of two fatty acid segments, (S)-malic acid was used as the chiral source to introduce (2S)- configuration. A known chiral cyclopropane derivative was introduced in the segment of cepaciamide A. The formation of (Z)-olefin in the segment of cepaciamide B was achieved by means of partial reduction of the acetylenic bond. Esterification between the fatty acid-segments and the amide-segment with DCC/DMAP and subsequent oxidative deprotection of the MPM group with CAN gave cepaciamides.
