A chemoenzymatic synthesis of the cis-decalin core associated with the novel anti-mitotic agent phomopsidin: Some observations concerning a high-pressure-promoted diels-alder cycloaddition reaction of (1S,2R)-3-methyl-cis-1,2-dihydrocatechol and the anionic oxy-cope rearrangement of compounds derived from the adduct

Australian Journal of Chemistry

Volumn 57, Issue 7, 2004, Pages 641-644

  Banwell, Martin G ^a   Edwards, Alison J ^a   McLeod, Malcolm D ^a   Stewart, Scott G ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

BIOASSAY; CHEMICAL BONDS; DERIVATIVES; ENZYMES; FUNGI; SPECTROSCOPIC ANALYSIS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

CHIRALITY; ENANTIOMERS; FUNGUS INDUCED DEFORMATIONS; LACTONE;

ORGANIC COMPOUNDS;

EID: 3242735973     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH04036     Document Type: Article

References (22)

1. M. Namikoshi, H. Kobayashi, T. Yoshimoto, T. Hosoya, J. Antibiot. 1997, 50, 890.
2. H. Kobayashi, S. Meguro, T. Yoshiraoto, M. Namikoshi, Tetrahedran 2003, 59, 455. doi:10.1016/S0040-4020(02)01566-1
3. F. Wakui, K. Harimaya, M. Iwata, R. Sashita, N. Chiba, T. Mikawa, Jpn. Kokai, Tokkyo Koho JP 07 126 211 1995 [Chem. Abstr. 1995, 123, 105272b].
4. F. Wakui, K. Harimaya, M. Iwata, R. Sashita, N. Chiba, T. Mikawa, Jpn. Kokai, Tokkyo Koho JP 07 126 211 1995 [Chem. Abstr. 1995, 123, 105272b].
5. [1,2]
6. (a) M. G. Banwell, J. R. Dupuche, Chem. Commun. 1996, 869. doi:10.1039/CC9960000869
7. (b) M. G. Banwell, J. R. Dupuche, R. W. Gable, Aust. J. Chem. 1996, 49, 639.
8. (c) M. G. Banwell, D. C. R. Hockless, J. W. Holman, R. W. Longmore, K. J. McRae, H. T. T. Pham, Synlett 1999, 1491.
9. For an excellent review on methods for generating cis-1,2- dihydrocatechols by microbial dihydroxylation of the corresponding aromatics as well the synthetic applications of these metabolites see: T. Hudlicky, D. Gonzalez, D. T. Gibson, Aldrichimica Acta 1999, 32, 35.
10. (a) M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle, Pure Appl. Chem. 2003, 75, 223.
11. (b) M. G. Banwell, D. C. R. Hockless, M. D. McLeod, New J. Chem. 2003, 27, 50. doi:10.1039/B206372G
12. (c) M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, Tetrahedron 2004, 60, 535. doi:10.1016/J.TET.2003.10.122
13. (a) M. G. Banwell, C. Chun, A. J. Edwards, M. M. Vögtle, Aust. J. Chem. 2003, 56, 861. doi:10.1071/CH03112
14. (b) D. Appels, M. G. Banwell, A. J. Edwards, G. J. Harfoot, D. C. R. Hockless, K. J. McRae, H. Schuhbauer, S. G. Stewart, A. C. Willis, unpublished.
15. (a) S. D. Kahn, W. J. Hehre, J. Am. Chem. Soc. 1987, 109, 663.
16. For recent reviews dealing with such effects see: (b) J. M. Coxon, R. D. J. Froese, B. Ganguly, A. P. Marchand, K. Morokuma, Synlett 1999, 1681. (c) G. Mehta, R. Uma, Acc. Chem. Res. 2000, 33, 278. doi:10. 1021/AR990123S
17. For recent reviews dealing with such effects see: (b) J. M. Coxon, R. D. J. Froese, B. Ganguly, A. P. Marchand, K. Morokuma, Synlett 1999, 1681. (c) G. Mehta, R. Uma, Acc. Chem. Res. 2000, 33, 278. doi:10. 1021/AR990123S
18. For examples of thermally induced reactions of cis-1,2-dihydrocatechols which proceed in a syn-selective fashion see: J. R. Gillard, D. J. Burnell, J. Chem. Soc., Chem. Commun. 1989, 1439. doi:10.1039/C39890001439
19. L. A. Paquette, Q. Zeng, Tetrahedron Lett. 1999, 40, 3823. doi: 10.1016/50040-4039(99)00631-0
20. Atomic coordinates, bond lengths and angles, displacement parameters, and other details associated with this analysis have been deposited at the Cambridge Crystallographic Data Centre (CCDC reference number 230238).
21. V. Moliner, R. Castillo, V. S. Safont, M. Oliva, S. Bohn, I. Tunon, J. Andres, J. Am. Chem. Soc. 1997, 119, 1941, and references therein. doi:10.1021/JA962571Q
22. J. P. Schaefer, J. J. Bloomfield, Org. React. 1967, 15, 1.