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 journalArticle

27 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)1073-1083
Number of pages11
JournalJournal of Natural Products
Volume70
Issue number7
DOIs
StatePublished - Jul 2007

Fingerprint

antineoplastic agents
Depsipeptides
Antineoplastic Agents
synthetic products
synthesis
transesterification
stereochemistry
cell growth
Growth Inhibitors
Stereochemistry
alcohols
antibiotics
Transesterification
Cell growth
Biological Products
Alcohols
Anti-Bacterial Agents
respirantin
Neoplasms
neoplasm cells

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Pettit, G., Smith, T. H., Feng, S., Knight, J. C., Tan, R., Pettit, R., & Hinrichs, P. A. (2007). Antineoplastic agents. 561. Total synthesis of respirantin. Journal of Natural Products, 70(7), 1073-1083. https://doi.org/10.1021/np0680735

Antineoplastic agents. 561. Total synthesis of respirantin. / Pettit, George; Smith, Thomas H.; Feng, Song; Knight, John C.; Tan, Rui; Pettit, Robin; Hinrichs, Peter A.

In: Journal of Natural Products, Vol. 70, No. 7, 07.2007, p. 1073-1083.

Research output: Contribution to journalArticle

Pettit, G, Smith, TH, Feng, S, Knight, JC, Tan, R, Pettit, R & Hinrichs, PA 2007, 'Antineoplastic agents. 561. Total synthesis of respirantin', Journal of Natural Products, vol. 70, no. 7, pp. 1073-1083. https://doi.org/10.1021/np0680735
Pettit, George ; Smith, Thomas H. ; Feng, Song ; Knight, John C. ; Tan, Rui ; Pettit, Robin ; Hinrichs, Peter A. / Antineoplastic agents. 561. Total synthesis of respirantin. In: Journal of Natural Products. 2007 ; Vol. 70, No. 7. pp. 1073-1083.
@article{37bb64137ed9474ba176b1f68c5111e7,
title = "Antineoplastic agents. 561. Total synthesis of respirantin",
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.",
author = "George Pettit and Smith, {Thomas H.} and Song Feng and Knight, {John C.} and Rui Tan and Robin Pettit and Hinrichs, {Peter A.}",
year = "2007",
month = "7",
doi = "10.1021/np0680735",
language = "English (US)",
volume = "70",
pages = "1073--1083",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "7",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=34548023267&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34548023267&partnerID=8YFLogxK

U2 - 10.1021/np0680735

DO - 10.1021/np0680735

M3 - Article

VL - 70

SP - 1073

EP - 1083

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 7

ER -