抗肿瘤药。561. 呼吸定的全合成。
Antineoplastic agents. 561. Total synthesis of respirantin.
作者信息
Pettit George R, Smith Thomas H, Feng Song, Knight John C, Tan Rui, Pettit Robin K, Hinrichs Peter A
机构信息
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, PO Box 872404, Tempe, Arizona 85287-2404, USA.
出版信息
J Nat Prod. 2007 Jul;70(7):1073-83. doi: 10.1021/np0680735. Epub 2007 Jul 4.
Total synthesis of the 18-membered ring cyclodepsipeptide believed to be respirantin (1b) has been achieved. The key step in the synthesis is an intramolecular transesterification of the beta-ketoester alcohol 6 to afford the protected macrocycle 5. The synthetic product was shown to be identical to a natural product presumed to be respirantin (1b), and the absolute stereochemistry of six of the seven asymmetric centers of cyclodepsipeptide 1b was unequivocally established. Respirantin (1b) was found to be a remarkable inhibitor of cancer cell growth and related to the antimycin family of antibiotics.
已完成对被认为是呼吸抑素（1b）的18元环缩肽的全合成。合成中的关键步骤是β-酮酯醇6的分子内酯交换反应，以得到受保护的大环化合物5。合成产物被证明与推测为呼吸抑素（1b）的天然产物相同，并且明确确定了环缩肽1b的七个不对称中心中六个的绝对立体化学。发现呼吸抑素（1b）是癌细胞生长的显著抑制剂，并且与抗生素抗霉素家族有关。
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