Antineoplastic agents. 561. Total synthesis of respirantin

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

doi:10.1021/np0680735

Antineoplastic agents. 561. Total synthesis of respirantin

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

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	1073-1083
Number of pages	11
Journal	Journal of Natural Products
Volume	70
Issue number	7
DOIs	https://doi.org/10.1021/np0680735
State	Published - Jul 2007

ASJC Scopus subject areas

Analytical Chemistry
Molecular Medicine
Pharmacology
Pharmaceutical Science
Drug Discovery
Complementary and alternative medicine
Organic Chemistry

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10.1021/np0680735

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abstract = "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.",

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T1 - Antineoplastic agents. 561. Total synthesis of respirantin

AU - Pettit, George

AU - Smith, Thomas H.

AU - Feng, Song

AU - Knight, John C.

AU - Tan, Rui

AU - Pettit, Robin

AU - Hinrichs, Peter A.

PY - 2007/7

Y1 - 2007/7

N2 - 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.

AB - 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.

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Antineoplastic agents. 561. Total synthesis of respirantin

Abstract

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