Application of the reaction of D-glucose with meldrum's acid: Total synthesis of the styryl lactones (+)-goniofufurone and (+)-7-epi- goniofufurone

Tetrahedron

Volumn 55, Issue 32, 1999, Pages 9793-9800

  Bruns, Rainer ^a   Wernicke, Angelika ^a   Köll, Peter ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

Acetogenins; Carbohydrates; Lactones; Meldrum's acid

Indexed keywords

7 EPIGONIOFUFURONE; ACETAL DERIVATIVE; ACID; ALDEHYDE; BROMIDE; GLUCOSE; GONIOFUFURONE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

ARTICLE; CHEMICAL REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033529647     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00535-9     Document Type: Article

References (23)

1. Wu, Y.C.; Duh, C.Y.; Chang, F.R.; Chang, G.Y.; Wang, S.K.; Chang, J.J.; McPhail, D.R.; McPhail, A.T.; Lee, K.H.; J. Nat. Prod. 1991, 54, 1077.
2. Talapatra, S.K.; Basu, D.; Deb, T.; Goswami, S.; Talapatra, B.; Indian. J. Chem., Sect. B. 1985, 24, 29.
3. Sam, T.W.; Yeu, C.S.; Matsjeh, S.; Gan, E.K.; Razak, D.; Mohamed, A.L.; Tetrahedron Lett. 1987, 28, 2541.
4. Fang, X.P.; Anderson, J.E.; Chang, C.-J.; Fanwick, P.E.; McLaughlin, J.L.; J. Chem. Soc., Perkin Tras. 1 1990, 1655.
5. Fang, X.P.; Anderson, J.E.; Chang, C.-J.; McLaughlin, J.L.; J. Nat. Prod. 1991, 54, 1034.
6. a) Shing, T.K.M.; Tsui, H.-C.; J. Chem. Soc., Chem. Commun. 1992, 432,
7. b) Shing, T.K.M.; Tsui, H.-C.; Zhou, Z.-H.; Tetrahedron 1992, 48, 8659.
8. a) Gracza, T.; Jäger, V.; Synlett 1992, 191,
9. b) Gracza, T.; Jäger, V.; Synthesis 1994, 1359.
10. a) Shing, T.K.M.; Tsui, H.C.; Zhou, Z.-H.; J. Org. Chem. 1995, 60, 3121 and references cited therein,
11. b) Mukai, C.; Hirai, S.; Kim, I.J.; Kido, M.; Hanaoka, M.; Tetrahedron 1996, 52, 6547,
12. c) Tsubuki, M.; Kanai, K.; Nagase, H.; Honda, T.; Tetrahedron 1999, 55, 2493 and references cited therein,
13. d) Surivet, J.P.; Vatèle, J.-M.; Tetrahedron Lett. 1996, 37, 4373,
14. e) Mereyala, H.B.; Gadikota, R.R.; Krishnan, R.; J. Chem. Soc., Perkin Trans. 1 1997, 3567,
15. f) Surivet, J.P.; Vatèle, J.-M.; Tetrahedron Lett. 1997, 38, 819,
16. g) Cagnolini, C.; Ferri, M.; Jones, P.R.; Murphy, P.J.; Ayres, B.; Cox, B.; Tetrahedron 1997, 53, 4815,
17. h) Yi, X.-H.; Meng, Y.; Li, C.-J.; J. Chem. Soc., Chem. Commun. 1998, 449,
18. i) Yi, X.-H.; Meng, Y.; Hua, X.-G.; Li, C.-J.; J. Org. Chem. 1998, 63, 7472.
19. a) Zamora Mata, F.; Martinez, M.B.; Perez, J.A.G.; Carbohydr. Res. 1990, 210, 223,
20. b) Zamora Mata, F.; Martinez, M.B.; Perez, J.A.G.; Carbohydr. Res. 1992, 225, 159,
21. c) Wernicke, A.; Lützen, A.; Kovács, J.; Köll, P.; Eur. J. Org. Chem. submitted.
22. Hoye, T.R.; Tan, L.; Tetrahedron Lett. 1995, 36, 1981.
23. Richtmyer, N.K.; Methods in Carbohydrate Chemistry 1963, 2, 320.