|
Studies Directed Towards the Preparation of Probes for the Photoaffinity Labelling of Gibberellin Receptors
†
James R.
Crow A,
Peter M.
Chandler B and
Lewis N.
Mander A C
A
Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.
B
CSIRO Plant Industry, GPO Box 1600, Canberra, ACT 2601, Australia.
C
Corresponding author. Email: mander@rsc.anu.edu.au
Australian Journal of Chemistry
64(4)
471-488 http://dx.doi.org/10.1071/CH10441
Submitted: 3 December 2010 Accepted: 17 February 2011 Published:
18
April
2011
|  |
|
|
Abstract
Model studies for the preparation of photoaffinity probes designed to explore the nature of gibberellin receptor sites have provided a wide range of gibberellin derivatives that should afford useful scaffolds incorporating auxiliary groups attached to C-2 and C-12. Methodology features the stereocontrolled opening of 2β,3β-epoxy gibberellins by attack on the lower face at C-2, while functionalization of C-12 was effected by the rhodium acetate-catalyzed CH insertion reaction of a 17-diazo ketone. Compounds were screened for bioactivity in growth and barley endosperm-based bioassays. 
|
References
[1]
M. Ueguchi-Tanaka, M. Ahikari, M. Nakajima, H. Itoh, E. Katoh, M. Kobayashi, T.-Y. Chow, C. Hsing, H. Kitano, I. Yamaguchi, M. Matsuoka, Nature 2005, 437, 693. | CrossRef | CAS | PubMed | 
[2]
M. Nakajima, A. Shimada, Y. Takashi, Y. C. Kim, S. H. Park, M. Ueguchi-Tanaka, H. Suzuki, E. Katoh, S. Iuchi, M. Kobayashi, T. Maeda, M. Matsuoka, I. Yamaguchi, Plant J. 2006, 46, 880. | CrossRef | CAS | PubMed |
[3]
R. Hooley, M. H. Beale, S. J. Smith, Planta 1991, 183, 274. | CrossRef | CAS |
[4]
R. Hooley, Plant Mol. Biol. 1994, 26, 1529. | CrossRef | CAS | PubMed |
[5]
S. Gilroy, R. L. Jones, Plant Physiol. 1994, 104, 1185. | CAS | PubMed |
[6]
P. M. Chandler, C. A. Harding, A. R. Ashton, M. D. Mulcair, N. E. Dixon, L. N. Mander, Molecular Plant 2008, 1, 285. | CrossRef | CAS | PubMed |
[7]
S. A. Fleming, Tetrahedron 1995, 51, 12479. | CrossRef | CAS |
[8]
M. H. Beale, R. Hooley, M. J. Lewis, S. J. Smith, J. L. Ward, J. Chem. Soc., Perkin Trans. 1 1995, , 657. | CrossRef | CAS |
[9]
R. Hooley, M. H. Beale, Planta 1991, 183, 274. | CrossRef | CAS |
[10]
M. Nassal, J. Am. Chem. Soc. 1984, 106, 7540. | CrossRef | CAS |
[11]
Y. Hatanaka, H. Hashimoto, H. Kurihara, H. Nakayama, Y. Kanaoka, J. Org. Chem. 1994, 59, 383. | CrossRef | CAS |
[12]
M. Hashimoto, Y. Kanaoka, Y. Hatanaka, Heterocycles 1997, 46, 215. | CrossRef | CAS |
[13]
T. Weber, J. Brunner, J. Am. Chem. Soc. 1995, 117, 3084. | CrossRef | CAS |
[14]
L. N. Mander, Chem. Rev. 1992, 92, 573. | CrossRef | CAS |
[15]
M. J. McDonough, P. M. Chandler, unpublished results.
[16]
P. M. Chandler, M. Robertson, Plant Physiol. 1999, 120, 623. | CrossRef | CAS | PubMed |
[17]
L. N. Mander, J. V. Turner, Tetrahedron Lett. 1981, 22, 4149. | CrossRef | CAS |
[18]
D. Yang, M. K. Wong, Y. C. Yip, J. Org. Chem. 1995, 60, 3887. | CrossRef | CAS |
[19]
1H NMR spectra of the 2α,3α-diastereomer agree with those reported by L. J. Beely, J. MacMillan, J. Chem. Soc. Perkin
1976, 1, 1022.
[20]
S. Chandrasekhar, Ch. Raji Reddy, B. Nagendra Babu, G. Chandrashekar, Tetrahedron Lett. 2002, 43, 3801. | CrossRef | CAS |
[21]
P. A. Bartlett, W. S. Johnson, Tetrahedron Lett. 1970, 51, 4459. | CrossRef |
[22]
L. Lombardo, L. N. Mander, J. V. Turner, J. Am. Chem. Soc. 1980, 102, 6626. | CrossRef | CAS |
[23]
P. S. Kirkwood, J. MacMillan, M. Hutchison, J. Chem. Soc. Perkin 1982, 1, 707. | CrossRef |
[24]
L. N. Mander, Nat. Prod. Rep. 2003, 20, 49. | CrossRef | CAS | PubMed |
[25]
T. Ye, M. A. McKervey, Chem. Rev. 1994, 94, 1091. | CrossRef | CAS |
[26]
P. S. Grieco, S. Gilman, M. Nishizawa, J. Org. Chem. 1976, 41, 1485. | CrossRef | CAS |
[27]
A. S.-H. Lee, Y.-J. Hu, S. F. Chu, Tetrahedron 2001, 57, 2121. | CrossRef |
|
|
 |
Subscriber Login |
 |
|
e-Alerts
Connect with us
