Asymmetric synthesis of cis-7-methoxycalamenene via the intramolecular buchner reaction of an α-diazoketone

Journal of Organic Chemistry

Volumn 77, Issue 4, 2012, Pages 2035-2040

  McDowell, Paul A ^a   Foley, David A ^a   O'Leary, Patrick ^a,b   Ford, Alan ^a   Maguire, Anita R ^a  

^a UNIVERSITY COLLEGE CORK   (Ireland)

^b NATIONAL UNIVERSITY OF IRELAND   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC SYNTHESIS; BICYCLIC RING SYSTEM; DIAZOKETONES; REACTION SEQUENCES; SYNTHETIC ROUTES;

CHEMISTRY;

ORGANIC COMPOUNDS;

7 METHOXYCALAMENENE; ACID; ALPHA DIAZOKETONE; AZULENOL; AZULENONE; DIHYDRONAPHTHALENE; KETONE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ENANTIOMER; INTRAMOLECULAR BUCHNER REACTION; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

AZULENES; CATALYSIS; CYCLIZATION; KETONES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NAPHTHALENES; SESQUITERPENES; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM; TERPENES;

EID: 84857206301     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202499j     Document Type: Article

References (26)

1. Constantino, A.; Linstrumelle, G.; Julia, S. Bull. Soc. Chim. Fr. 1970, 3, 907-912
2. Maguire, A. R.; Buckley, N. R.; O'Leary, P.; Ferguson, G. Chem Commun. 1996, 2595-2596
3. Maguire, A. R.; Buckley, N. R.; O'Leary, P.; Ferguson, G. J. Chem. Soc., Perkin Trans. 1 1998, 4077-4091
4. Maguire, A. R.; O'Leary, P.; Harrington, F.; Lawrence, S. E.; Blake, A. J. J. Org. Chem. 2001, 66, 7166-7177
5. O'Keeffe, S.; Harrington, F.; Maguire, A. R. Synlett 2007, 15, 2367-2370
6. O'Neill, S.; O'Keeffe, S.; Harrington, F.; Maguire, A. R. Synlett 2009, 14, 2312-2314
7. McNamara, O. A.; Maguire, A. R. Tetrahedron 2011, 67 (1) 9-40
8. Maier, G. Angew. Chem., Int. Ed. Engl. 1967, 6, 402-413
9. Foley, D. A.; Maguire, A. R. Tetrahedron 2010, 66 (6) 1131-1175
10. Reisman, S. E.; Nani, R. R.; Levin, S. Synlett 2011, 17, 2437-2442
11. Salmoun, M.; Braekman, J. C.; Ranarivelo, Y.; Rasamoelisendra, R.; Ralambomanana, D.; Dewelle, J.; Darro, F.; Kiss, R. Nat. Prod. Res. 2007, 21 (2) 111-120
12. Nabeta, K.; Katayama, K.; Nakagawara, S.; Katoh, K. Phytochemistry 1992, 32, 117-122
13. Brenna, E.; Dei Negri, C.; Fuganti, C.; Gatti, F. G.; Serra, S. Tetrahedron: Asymmetry 2004, 15, 335-340
14. Alexander, J.; Rao, G. S. K. Tetrahedron 1971, 27, 645-651
15. Uemura, M.; Isobe, K.; Take, K.; Hayashi, Y. J. Org. Chem. 1983, 48, 3855-3858
16. Liao, S.; Shenderovich, M. D.; Lin, J.; Hruby, V. J. Tetrahedron 1997, 53, 16645-16662
17. Liao, S.; Han, Y.; Qiu, W.; Bruck, M.; Hruby, V. J. Tetrahedron Lett. 1996, 37, 7917-7920
18. Lin, J.; Liao, S.; Han, Y.; Qiu, W.; Hruby, V. J. Tetrahedron: Asymmetry 1997, 8, 3213-3221
19. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141-6144
20. Arndt, F.; Eistert, B.; Partale, W. Ber. Dtsch. Chem. Ges. 1927, 60B, 1364-1370
21. Tanaka, J.; Miyake, T.; Iwasaki, N.; Adachi, K. Bull. Chem. Soc. Jpn. 1992, 65, 2851-2853
22. McCormick, J. P.; Pachlatko, J. P.; Schafer, T. R. Tetrahedron Lett. 1978, 3993-3994
23. Benincori, T.; Bruno, S.; Celentano, G.; Pilati, T.; Ponti, A.; Rizzo, S.; Sada, M.; Sannicolo, F. Helv. Chim. Acta 2005, 88, 1776-1789
24. Pirrung, M. C.; Han, H.; Ludwig, R. T. J. Org. Chem. 1994, 59, 2430-2436
25. Arndt, F. Organic Syntheses; Wiley: New York, 1943; Coll. Vol. 2, p 461.
26. Marshall, J. A.; Partridge, J. J. J. Org. Chem. 1968, 33, 4090-4097