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Antineoplastic agents. 561. Total synthesis of respirantin

Journal of Natural Products, ISSN: 0163-3864, Vol: 70, Issue: 7, Page: 1073-1083
2007
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Article Description

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 β-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. © 2007 American Chemical Society and American Society of Pharmacognosy.

Bibliographic Details

Pettit, George R; Smith, Thomas H; Feng, Song; Knight, John C; Tan, Rui; Pettit, Robin K; Hinrichs, Peter A

American Chemical Society (ACS)

Chemistry; Biochemistry, Genetics and Molecular Biology; Pharmacology, Toxicology and Pharmaceutics; Medicine

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