Stereospecific synthesis of tabtoxin
Publication type: Journal Article
Publication date: 1984-01-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Tabtoxin (1), the exotoxin fromPseudmonas tabaci (the organism responsible for Wildfire disease of tobacco plants), has been synthesised by a stereospecific route. The cycloaddition of an acylnitroso compound to a cyclohexadiene proceeded regioselectively to give the bicyclic ester (6), which was transformed to the amine (24) through reductive amination of the aldehyde (10). Oxidative cleavage of the olefin (25) gave the corresponding diacid (26), whose functional groups were appropriately differentiated by formation of the peptide (29). Cyclisation of the β-amino acid (30) and subsequent hydrogenolysis of the resulting spiro β-lactam (31) gave tabtoxin.
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Metrics
28
Total citations:
28
Citations from 2024:
1
(3.57%)
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MLA
Cite this
GOST
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BALDWIN J. E. et al. Stereospecific synthesis of tabtoxin // Tetrahedron. 1984. Vol. 40. No. 19. pp. 3695-3708.
GOST all authors (up to 50)
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BALDWIN J. E., D Bailey P., GALLACHER G., OTSUKA M., Singleton K. A., Wallace P. M., Prout K., Wolf W. M. Stereospecific synthesis of tabtoxin // Tetrahedron. 1984. Vol. 40. No. 19. pp. 3695-3708.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/s0040-4020(01)88799-8
UR - https://doi.org/10.1016/s0040-4020(01)88799-8
TI - Stereospecific synthesis of tabtoxin
T2 - Tetrahedron
AU - BALDWIN, JACK E.
AU - D Bailey, Patrick
AU - GALLACHER, GERARD
AU - OTSUKA, MASAMI
AU - Singleton, Kevin A
AU - Wallace, Philip M.
AU - Prout, Keith
AU - Wolf, Wojaech M
PY - 1984
DA - 1984/01/01
PB - Elsevier
SP - 3695-3708
IS - 19
VL - 40
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1984_BALDWIN,
author = {JACK E. BALDWIN and Patrick D Bailey and GERARD GALLACHER and MASAMI OTSUKA and Kevin A Singleton and Philip M. Wallace and Keith Prout and Wojaech M Wolf},
title = {Stereospecific synthesis of tabtoxin},
journal = {Tetrahedron},
year = {1984},
volume = {40},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/s0040-4020(01)88799-8},
number = {19},
pages = {3695--3708},
doi = {10.1016/s0040-4020(01)88799-8}
}
Cite this
MLA
Copy
BALDWIN, JACK E., et al. “Stereospecific synthesis of tabtoxin.” Tetrahedron, vol. 40, no. 19, Jan. 1984, pp. 3695-3708. https://doi.org/10.1016/s0040-4020(01)88799-8.