Synthesis of the 3-methylene-2-vinyltetrahydropyran unit; the hallmark of the sesquiterpene, hodgsonox

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2470-2475

  Barlow, Anna J ^a   Compton, Benjamin J ^a   Weavers, Rex T ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBON; METABOLITES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

3-METHYLENE-2-VINYLTETRAHYDROPYRAN UNIT; CYCLIZATION; ELECTROPHILIC SITE; VINYL GROUP;

ORGANIC COMPOUNDS;

ACROLEIN; HODGSONOX; PYRAN DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; LIVERWORT; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; PYRANS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET; VINYL COMPOUNDS;

EID: 17044429000     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047998r     Document Type: Article

References (19)

1. Ainge, G. A.; Gerrard, P. J.; Hinkley, S. F.; Lorimer, S. D.; Weavers, R. T. J. Org. Chem. 2001, 66, 2818-2821.
2. Barlow, A. J.; Lorimer, S. D.; Morgan, E. R.; Weavers, R. T. Phytochemistry 2003, 63, 25-29.
3. Gerard, P. J.; Ruf, L. D.; Lorimer, S. D.; Heath, A. G. C. N. Z. J. Agric. Res. 1997, 40, 261-267.
4. Smith, A. B., III; Levenberg, P. A.; Jerris, P. J.; Scarborough, R. M.; Wovkulich, P. M. J. Am. Chem. Soc. 1981, 103, 1501-1513.
5. Takahashi, T.; Takehira, Y. In U.S. Patent 5180844, Daiso Co., Ltd., Osaka, Japan, 1993.
6. Dulcere, J.-P.; Baret, N.; Rodriguez, J. Synlett 1995, 923-924. Baret, N.; Dulcere, J.-P.; Rodriguez, J.; Pons, J.-M.; Fayre, R. Eur. J. Org. Chem. 2000, 1507-1516.
7. Dulcere, J.-P.; Baret, N.; Rodriguez, J. Synlett 1995, 923-924. Baret, N.; Dulcere, J.-P.; Rodriguez, J.; Pons, J.-M.; Fayre, R. Eur. J. Org. Chem. 2000, 1507-1516.
8. Flower, K. R.; Howard, V. J.; Naguthney, S.; Pritchard, R. G.; Warren, J. E.; McGown, A. T. Inorg. Chem. 2002, 41, 1907-1912.
9. Hiyama, T.; Wakasa, N.; Ueda, T.; Kusumoto, T. Bull. Chem. Soc. Jpn. 1990, 63, 640-642.
10. Havens, S. J.; Hergenrother, P. M. J. Org. Chem, 1985, 50, 1763-1765.
11. Smith, N. D.; Mancuso, J.; Lautens, M. Chem. Rev. 2000, 100, 3257-3282.
12. Zhang, H. X.; Guibe, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857-1867.
13. Kraus, G. A.; Molina, M. T.; Walling, J. A. J. Chem. Soc., Chem. Commun. 1986, 1568-1569.
14. Kozmin, S. A. Org. Lett. 2001, 3, 755-758.
15. Morgenlie, S. Acta Chem. Scand. 1971, 1154-1155.
16. Imai, T.; Nishida, S. J. Org. Chem. 1990, 55, 4849-4852.
17. Huet, F.; Lechevallier, A.; Pellet, M.; Conia, J. M. Synthesis 1978, 1, 63-65.
18. Sinha, S. C.; Sinha, S. C.; Keinan, E. J. Org. Chem. 1999, 64, 7067-7073.
19. Brown, R. C.; Phadke, A. S. Synlett 1993, 927-928.