Isopropenyldihydrofuran Derivatives. Preparation and Reactions of Some Isopropenyldihydrofurandicarboxylates

Journal of Heterocyclic Chemistry

Volumn 34, Issue 4, 1997, Pages 1329-1334

  Yamaguchi, Seiji ^a   Sugioka, Yoshihiko ^a   Ishida, Miwa ^a   Yokoyama, Hajime ^a   Hirai, Yoshiro ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0004930525     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340439     Document Type: Article

References (11)

1. (-)-Tremetone: W. A. Bonner, N. I. Burke, W. E. Fleck, R. K. Hill, J. A. Joule, B. Sjoberg, and J. H. Zalkow, Tetrahedron, 20, 1419 (1964); (-)-Hydroxytremetone and (+)-marmesin: I. Harada, Y. Hirose, and M. Nakazaki, Tetrahedron Letters, 52, 5463 (1968); (+)-Fomannoxin: Y. Kawase, S. Yamaguchi, O. Inoue, M. Sannomiya, and K. Kawabe, Chem. Letters, 1581 (1980).
2. (-)-Tremetone: W. A. Bonner, N. I. Burke, W. E. Fleck, R. K. Hill, J. A. Joule, B. Sjoberg, and J. H. Zalkow, Tetrahedron, 20, 1419 (1964); (-)-Hydroxytremetone and (+)-marmesin: I. Harada, Y. Hirose, and M. Nakazaki, Tetrahedron Letters, 52, 5463 (1968); (+)-Fomannoxin: Y. Kawase, S. Yamaguchi, O. Inoue, M. Sannomiya, and K. Kawabe, Chem. Letters, 1581 (1980).
3. (-)-Tremetone: W. A. Bonner, N. I. Burke, W. E. Fleck, R. K. Hill, J. A. Joule, B. Sjoberg, and J. H. Zalkow, Tetrahedron, 20, 1419 (1964); (-)-Hydroxytremetone and (+)-marmesin: I. Harada, Y. Hirose, and M. Nakazaki, Tetrahedron Letters, 52, 5463 (1968); (+)-Fomannoxin: Y. Kawase, S. Yamaguchi, O. Inoue, M. Sannomiya, and K. Kawabe, Chem. Letters, 1581 (1980).
4. J. Nickl, Chem, Ber., 91, 553 (1958); in this paper, the product in the cyclization of 3-oxobutate with 1,4-dibromo-2-methyl-2-butene was described as 2-isopropenyl-1-acetylcyclopropane-1-carboxylate, but this might be revised to the 4-isopropenyl-2-methyl-4,5-dihydrofuran-3-carboxylate.
5. Diethyl 2-oxosuccinate was used as the commercially available sodium enolate (diethyl oxalacetate, sodium salt).
6. Hydrolyses in warm alkaline solution might cause a decomposition of the furan ring, especially in 2,3-diester 1a.
7. Diels-Alder reactions of diester 1a with some dienes were unsuccessful.
8. S. Nahm and S. M. Weinreb,. Tetrahedron Letters, 22, 3815 (1981).
9. D. W. Brooks, L. D. L. Lu, and S. Masamune, Angew. Chem. Int. Ed. Engl., 18, 72 (1979).
10. N. McCarthy, M. A. McKervey, and T. Ye, Tetrahedron Letters, 33, 5983 (1992).
11. Half-ester 2b was readily decarboxylated in the thermal analyses.