Concise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition

Organic Letters

Volumn 4, Issue 10, 2002, Pages 1809-1811

  Hodgson, David M ^a   Avery, Thomas D ^a   Donohue, Andrew C ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 HYDROXY NEMORENSIC ACID; 4-HYDROXY-NEMORENSIC ACID; ANTINEOPLASTIC AGENT; DRUG DERIVATIVE; FURAN DERIVATIVE; NEMORENSIC ACID; PARGYLINE; PROPARGYL BROMIDE; PYRROLIZIDINE ALKALOID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SENECIO; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FURANS; MODELS, MOLECULAR; PARGYLINE; PYRROLIZIDINE ALKALOIDS; SENECIO; STEREOISOMERISM;

EID: 0037118362     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025917c     Document Type: Article

References (29)

1. (a) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II; Bird, C. W., Ed.; Pergamon Press: Oxford, 1996; Vol. 2, pp 351-393.
2. (b) Elliott, M. C.; Williams, E. J. Chem. Soc., Perkin, Trans. 1 2001, 2303-2340.
3. (a) Romo de Vivar, A.; Pérez, A.-L.; Arciniegas, A.; Vidales, P.; Gaviño, R.; Villaseñor, J. L. Tetrahedron 1995, 51, 12521-12528.
4. (b) Pérez-Castorena, A.-L.; Arciniegas, A.; Castro, A.; Villaseñor, J. L.; Toscano, R. A.; Romo de Vivar, A. J. Nat. Prod. 1997, 60, 1322-1325.
5. Liddell, J. R. Nat. Prod. Rep. 2001, 18, 441-447.
6. (a) Klein, L. L. J. Am. Chem. Soc. 1985, 107, 2573-2574.
7. (b) Dillon, M. P.; Lee, N. C.; Stappenbeck, F.; White, J. D. J. Chem. Soc., Chem. Commun. 1995, 1645-1646.
8. (c) Rodríguez, J. R.; Rumbo, A.; Castedo, L.; Mascareñas, J. L. J. Org. Chem. 1999, 64, 4560-4563.
9. (d) Honda, T.; Ishikawa, F. J. Org. Chem. 1999, 64, 5542-5546.
10. (e) Donohoe, T. J.; Guillermin, J.-B.; Frampton, C.; Walter, D. S. Chem. Commun. 2000, 465-466.
11. (f) Liu, B.; Moeller, K. D. Tetrahedron Lett. 2001, 42, 7163-7165.
12. (g) López, F.; Castedo, L.; Mascareñas, J. L. Chem. Eur. J. 2002, 8, 884-899.
13. Hodgson, D. M.; Bailey, J. M.; Villalonga-Barber, C.; Drew, M. G. B.; Harrison, T. J. Chem. Soc., Perkin Trans. 1 2000, 3432-3443.
14. The "cis" terminology refers to the cis relationship of the C-3 Me and the two carboxylic acid groups.
15. (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223-269.
16. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998; Chapter 7.
17. Padwa, A.; Fryxell, G. E.; Zhi, L. J. Am. Chem. Soc. 1990, 112, 3100-3109.
18. During the course of our work, α-methyl α-diazoketones were shown to undergo tandem ylide formation-cycloaddition: (a) Muthusamy, S.; Babu, S. A.; Gunanathan, C.; Suresh, E.; Dastidar, P.; Jasra, R. V. Tetrahedron 2000, 56, 6307-6318.
19. (b) Wood, J. L.; Thompson, B. D.; Yusuff, N.; Pflum, D. A.; Matthäus, M. S. P. J. Am. Chem. Soc. 2001, 123, 2097-2098.
20. Marshall, J. A.; Partridge, J. J. J. Org. Chem. 1968, 33, 4090-4095.
21. 1H NMR) of the regioisomeric cycloadduct was generated which was easily removed by column chromatography.
22. Fleming, I.; Paterson, I. Synthesis 1979, 736-738.
23. CCDC 181801 available at http://www.ccdc.cam.ac.uk.
24. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
25. (b) Lusinchi, X.; Harquet, G. Tetrahedron 1997, 53, 13727-13738.
26. Nicolaou, K. C.; Duggan, M. E.; Ladduwahetty, T. Tetrahedron Lett. 1984, 25, 2069-2072.
27. CCDC 181906 available at http://www.ccdc.cam.ac.uk.
28. Hodgson, D. M.; Stupple, P. A.; Pierard, F. Y. T. M.; Labande, A. H.; Johnstone, C. Chem. Eur. J. 2001, 7, 4465-4476.
29. 2 at -10°C. Full details of this study will be reported in due course.