Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

Martin G. Banwell; Curtis F. Crasto; Christopher J. Easton; Tomislav Karoli; Darren R. March; Michael R. Nairn; Peter J. O’hanlon; Mark D. Oldham; Anthony C. Willis; Weimin Yue

doi:10.1039/b104890m

Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

Martin G. Banwell^*
, Curtis F. Crasto
, Christopher J. Easton
, Tomislav Karoli
, Darren R. March
, Michael R. Nairn
, Peter J. O’hanlon
, Mark D. Oldham
, Anthony C. Willis
, Weimin Yue

^*Corresponding author for this work

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

22 Citations (Scopus)

Abstract

The ketone (±)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (2)−21 and (+)−21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.

Original language	English
Pages (from-to)	2210-2211
Number of pages	2
Journal	Chemical Communications
Volume	1
Issue number	21
DOIs	https://doi.org/10.1039/b104890m
Publication status	Published - 2001

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10.1039/b104890m

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Banwell, M. G., Crasto, C. F., Easton, C. J., Karoli, T., March, D. R., Nairn, M. R., O’hanlon, P. J., Oldham, M. D., Willis, A. C., & Yue, W. (2001). Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues. Chemical Communications, 1(21), 2210-2211. https://doi.org/10.1039/b104890m

@article{2ecbd682db3e4e8990d5dfcee976503b,

title = "Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues",

abstract = "The ketone (±)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (2)−21 and (+)−21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.",

author = "Banwell, \{Martin G.\} and Crasto, \{Curtis F.\} and Easton, \{Christopher J.\} and Tomislav Karoli and March, \{Darren R.\} and Nairn, \{Michael R.\} and O{\textquoteright}hanlon, \{Peter J.\} and Oldham, \{Mark D.\} and Willis, \{Anthony C.\} and Weimin Yue",

year = "2001",

doi = "10.1039/b104890m",

language = "English",

volume = "1",

pages = "2210--2211",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "21",

}

Banwell, MG, Crasto, CF, Easton, CJ, Karoli, T, March, DR, Nairn, MR, O’hanlon, PJ, Oldham, MD, Willis, AC & Yue, W 2001, 'Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues', Chemical Communications, vol. 1, no. 21, pp. 2210-2211. https://doi.org/10.1039/b104890m

Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues. / Banwell, Martin G.; Crasto, Curtis F.; Easton, Christopher J. et al.
In: Chemical Communications, Vol. 1, No. 21, 2001, p. 2210-2211.

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

TY - JOUR

T1 - Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

AU - Banwell, Martin G.

AU - Crasto, Curtis F.

AU - Easton, Christopher J.

AU - Karoli, Tomislav

AU - March, Darren R.

AU - Nairn, Michael R.

AU - O’hanlon, Peter J.

AU - Oldham, Mark D.

AU - Willis, Anthony C.

AU - Yue, Weimin

PY - 2001

Y1 - 2001

N2 - The ketone (±)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (2)−21 and (+)−21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.

AB - The ketone (±)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (2)−21 and (+)−21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.

UR - https://www.scopus.com/pages/publications/0035824034

U2 - 10.1039/b104890m

DO - 10.1039/b104890m

M3 - Article

SN - 1359-7345

VL - 1

SP - 2210

EP - 2211

JO - Chemical Communications

JF - Chemical Communications

IS - 21

ER -

Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues

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