The sequential annulation of an arene with a tetrahydrofuran provides a new route to the pseudopterosins

Tetrahedron Letters

Volumn 40, Issue 47, 1999, Pages 8299-8300

  Harrowven, David C ^a   Sibley, Graham E M ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

Annulation; Cyclisation; Lactones; Natural products; Terpenes and Terpenoids

Indexed keywords

LACTONE; PSEUDOPTEROSIN; TERPENE DERIVATIVE; TERPENOID DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CYCLIZATION; PARTIAL DRUG SYNTHESIS;

EID: 0033584985     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01761-X     Document Type: Article

References (31)

1. a. Look, S.A.; Fenical. W.; Matsumoto, G.K.; Clardy, J. J. Org. Chem., 1986, 51, 5140;
2. b. Roussis, V.; Wu, Z.D.; Fenical, W.; Strobel, S.A.; Van Duyne, G.D.; Clardy, J. J. Org. Chem., 1990, 55, 4916;
3. c. Harvis, C.A.; Burch, M.T.; Fenical, W. Tetrahedron Lett., 1988, 29, 4361.
4. a. Ettouati, W.S.; Jacobs. R.S. Mol. Pharmacol., 1987, 31, 500;
5. b. Fenical, W. J. Nat. Prod., 1987, 50, 1001;
6. c. Potts, B.C.M.; Faulkner, D.J.; Jacobs, R.S. J. Nat. Prod., 1992, 55, 1701;
7. d. Rodríguez, A.D. Tetrahedron, 1995, 51, 4571;
8. e. Mayer. A.M.S.; Jacobson, P.B.; Fenical, W.; Jacobs. R.S.; Glaser, K.B. Life Sciences, 1998, 62, 401.
9. Rouhi, A.M. Chem. Eng. News, 1995, November 20, 42.
10. a. Kozikowski, A.P.; Wu, J.P. Synlett, 1991, 465;
11. b. Jung, M.S.; Siedem, C.S. J. Am. Chem. Soc., 1993, 115, 3822;
12. c. Harrowven, D.C.; Dennison, S.T.; Howes, P. Tetrahedron Lett., 1994, 35, 4243:
13. d. Schmalz, H.G.; Schwarz, A.; Dürner, G. Tetrahedron Lett., 1994, 37, 6861;
14. e. Schmalz, H.G.; Majdalani, A.; Geller, T.; Hollander J.; Bats, J.W. Tetrahedron Lett., 1995, 36, 4777;
15. f. Eklund, L.; Sarvary, I.; Frejd, T. J. Chem. Soc., Perkin Trans. 1, 1996, 303.
16. a. Broka, C.A.; Chan, S.; Peterson, B. J. Org. Chem., 1988, 53, 1584;
17. b. Corey, E.J.; Carpino, P. J. Am. Chem. Soc., 1989, 111, 5472;
18. c. Corey, E.J.; Carpino, P. Tetrahedron Lett., 1990, 31, 3857;
19. d. McCombie, S.W.; Cox, B.; Ganguly, A.K. Tetrahedron Lett., 1991, 32, 2087;
20. e. McCombie, S.W.; Ortiz, C.; Cox, B.; Ganguly, A.K. Synlett, 1993, 541;
21. f. Buszek, K.R.; Bixby, D.L. Tetrahedron Lett., 1995, 36, 9129;
22. g. Gill, S.; Kocienski, P.; Kohler, A.; Pontiroli, A.; Qun, L. Chem. Commun., 1996, 1743;
23. h. Majdalani. A.; Schmalz, H.G. Synlett, 1997, 1303;
24. i. Corey, E.J.; Lazerwith, S.E. J. Am. Chem. Soc., 1998, 120, 12777;
25. LeBrazidec, J.Y.; Kocienski, P.J.; Connolly, J.D.; Muir, K.W. J. Chem. Soc., Perkin Trans, 1, 1998, 2475.
26. a. Harrowven, D.C.; Dainty, R.F. Tetrahedron Lett., 1997, 38, 7123;
27. b. Segi, M.; Takebe, M.; Masuda, S.; Nakajima T.; Suga, S. Bull. Chem. Soc. Jpn., 1982, 55, 167;
28. c. Brauman, I.; Solladié-Cavallo, A. Chem. Commun., 1968, 1124.
29. Jäger, V.; Günther, H.J. Tetrahedron Lett., 1977, 29, 2543.
30. Barlett, P.A.; Myerson, J. J. Am. Chem. Soc., 1978, 100, 3950.
31. Brimble, M.A.; Edmonds, M.K. Tetrahedron, 1995, 51, 9995.