Intramolecular diels-alder reactions of 5-vinyl-1,3-cyclohexadienes

Organic Letters

Volumn 5, Issue 10, 2003, Pages 1701-1704

  Ng, Stephanie M ^a   Beaudry, Christopher M ^a   Trauner, Dirk ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DIELS ALDER REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 0041812577     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0343414     Document Type: Article

References (16)

1. (a) Roush, W. R. in Comprehensive Organic Synthesis; Trost, B. ed.; Vol. 5, pp 513 ff; Oxford: Pergamon Press 1991.
2. (b) Nicolaou, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem.-Int. Edit. 2002, 41, 1668.
3. (a) Jendralla, H.; Jelich, K.; Delucca, G.; Paquette, L. A. J. Am. Chem. Soc. 1986, 108, 3731.
4. (b) Maier, G.; Wiegand, N. H.; Baum, S.; Wullner, R.; Mayer, W.; Boese, R. Chem. Ber. 1989, 122, 767.
5. (c) Marvell, E. N.; Seubert, J.; Vogt, G.; Zimmer, G.; Moy, G.; Siegmann, J. R. Tetrahedron 1978, 34, 1323.
6. (d) ten Have, R.; van Leusen, A. M. Tetrahedron 1998, 54, 1913.
7. (e) Loeliger, P.; Mayer, H. Helv. Chim. Acta 1980, 63, 1604, and references therein.
8. Beaudry, C. M.; Trauner, D. Org. Lett. 2002, 4, 2221.
9. Lee, K.; Jackson, J. A.; Wiemer, D. F. J. Org. Chem. 1993, 58, 5967.
10. Alahiane, A.; Rochdi, A.; Taourirte, M.; Redwane, N.; Sebti, S.; Lazrek, H. B. Tetrahedron Lett. 2001, 42, 3579.
11. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
12. Pelletier, S. W.; Mody, N. V.; Djarmati, Z.; Lajsic, S. D. J. Org. Chem. 1976, 41, 3042.
13. Bohlmann, F.; Jakupovic, J.; Ahmed, M.; Grenz, M.; Suding, H.; Robinson, H.; King, R. M. Phytochemistry 1981, 20, 113.
14. For an account on pimarane diterpenes, see: Hanson, J. R. Nat. Prod. Rep. 2002, 19, 125, and previous reviews in this series.
15. For Diels-Alder reactions in Nature, see: Ose, T.; Watanabe, K.; Mie, T. ; Honma, M. Watanabe, H.; Yao, H.; Oikawa, H.; Tanaka, I. Nature 2003, 422, 185, and references therein.
16. Biosynthetically, trachylobanoic acid could also arise from a beyerane or kaurane type precursor through carbocationic intermediates.