Abbreviated synthesis of the C3-C14 (substituted 1,7-dioxaspiro[5.5]undec-3-ene) system of okadaic acid

Organic Letters

Volumn 1, Issue 3, 1999, Pages 451-453

  Dounay, Amy B ^a   Forsyth, Craig J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,7 DIOXASPIRO(5,5)UNDEC 3 ENE; 1,7-DIOXASPIRO(5,5)UNDEC-3-ENE; ALKENE; ENZYME INHIBITOR; LACTONE; OKADAIC ACID; SPIRO COMPOUND;

ARTICLE; CHEMISTRY; SYNTHESIS;

ALKENES; ENZYME INHIBITORS; LACTONES; OKADAIC ACID; SPIRO COMPOUNDS;

EID: 0033549659     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906615     Document Type: Article

References (18)

1. Isobe, M.; Ichikawa, Y.; Goto, T. Tetrahedron Lett. 1986, 27, 963.
2. Urbanek, R. A.; Sabes, S. F.; Forsyth, C. J. J. Am. Chem. Soc. 1998, 120, 2523.
3. Sabes, S. F.; Urbanek, R. A.; Forsyth, C. J. J. Am. Chem. Soc. 1998, 120, 2534.
4. Ley, S. V.; Humphries, A. C.; Eick, H.; Downham, R.; Ross, A. R.; Boyce, R. J.; Pavey, J. B. J.; Pietruszka J. J. Chem. Soc., Perkin Trans. 1 1998, 3907.
5. Marko, I. E.; Dobbs, A. P.; Scheirmann, V.; Chelle, F.; Bayston, D. J. Tetrahedron Lett. 1997, 38, 2899.
6. Marko, I. E.; Chelle, F. Tetrahedron Lett. 1997, 38, 2895.
7. Dankwardt, S. M.; Dankwardt, J.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983 and preceding papers in that issue.
8. Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851.
9. Ichikawa, Y.; Isobe, M.; Bai, D.-L.; Goto, T. Tetrahedron 1987, 43, 4737.
10. 3
11. All new compounds gave characterization data that are fully consistent with the structures assigned.
12. Yamaguchi, M.; Hirao, I. Tetrahedron Lett. 1983, 24, 391.
13. Davis, F. A.; Kumar, A. J. Org. Chem. 1992, 57, 3337.
14. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 29, 4139.
15. Chabala, J. C.; Vincent, J. E. Tetrahedron Lett. 1978, 937.
16. 1H NMR spectra of the crude conjugate addition products.
17. 4
18. 3 primary alcohol in 61% yield.