Synthesis of (±)-crispine A via a nitrosoalkene hetero-Diels-Alder addition to ethyl vinyl ether

Synthesis

Volumn , Issue 1, 2011, Pages 142-146

  Yioti, Efthymia G ^a   Mati, Ioulia K ^a   Arvanitidis, Athanassios G ^a   Massen, Zoe S ^a   Alexandraki, Elli S ^a   Gallos, John K ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

alkaloids; hetero Diels Alder reaction; hydrogenation; natural products; total synthesis

Indexed keywords

ALKALOIDS; HETERO-DIELS-ALDER; HETERO-DIELS-ALDER REACTIONS; NATURAL PRODUCTS; SIMPLE METHOD; TOTAL SYNTHESIS; VINYL ETHERS;

ETHERS; HYDROGENATION; METABOLITES; NITROGEN COMPOUNDS; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

1 (3 ETHOXYPROPYL) 6,7 DIMETHOXYISOCHROMAN; 3 ETHOXY 9,10 DIMETHOXY 2,3,7,11B TETRAHYDRO[1,2]OXAZINO[3,2 A]ISOQUINOLIN 6[1H]ONE; 3 HYDROXY 8,9 DIMETHOXY 2,3,6,10B TETRAHYDROPYRROLO[2,1 A]ISOQUINOLIN 5[1H]ONE; 3,8,9 TRIMETHOXY 2,3,6,10B TETRAHYDROPYRROLO[2,1 A]ISOQUINOLIN 5[1H]ONE; 8,9 DIMETHOXY 2,3,6,10B TETRAHYDROPYRROLO[2,1 A]ISOQUINOLIN 5[1H]ONE; ACETIC ACID; ALKENE DERIVATIVE; CARDUUS CRISPUS EXTRACT; CRISPINE A; ETHYLVINYL ETHER; HERBACEOUS AGENT; ISOCHROMAN DERIVATIVE; METHYL 2 [2 (6 ETHOXY 5,6 DIHYDRO 4H 1,2 OXAZIN 3 YL) 4,5 DIMETHOXYPHENYL]ACETATE; METHYL 2 [2 (6 ETHOXY 5,6 DIHYDRO 4H 1,2 OXAZIN 3 YL) 4,5 DIMETHOXYPHENYL]ETHANOL; METHYL 2 [2 [2 BROMO 1 (HYDROXYIMINO)ETHYL] 4,5 DIMETHOXYPHENYL]ACETATE; REAGENT; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BIOTRANSFORMATION; CARDUUS; CARDUUS CRISPUS; CYCLIZATION; DIELS ALDER REACTION; DRUG DETERMINATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; STEREOCHEMISTRY;

EID: 78650518687     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258333     Document Type: Article

References (40)

1. Zhang Q, Tu G, Zhao Y, Cheng T, Tetrahedron 2002 58 6795
2. Knölker H.-J, Agarwal S, Tetrahedron Lett. 2005 46 1173
3. Meyer N, Opatz T, Eur. J. Org. Chem. 2006 3997
4. King F D., Tetrahedron 2007 63 2053
5. Bailey K R., Ellis A J., Reiss R, Snape T J., Turner N J., Chem. Commun. 2007 3640
6. Axford L C., Holden K E., Hasse K, Banwell M G., Steglich W, Wagler J, Willis A C., Aust. J. Chem. 2008 61 80
7. Coldham I, Jana S, Watson L, Martin N G., Org. Biomol. Chem. 2009 7 1674
8. Chiou W.-H, Lin G.-H, Hsu C.-C, Chaterpaul S J., Ojima I, Org. Lett. 2009 11 2659
9. Szawkao J, Zawadzka A, Wojtasiewicz K, Leniewski A, Drabowicz J, Czarnocki Z, Tetrahedron: Asymmetry 2005 16 3619
10. Wu T R., Chong J M., J. Am. Chem. Soc. 2006 128 9646
11. Szawkao J, Czarnocki S J., Zawadzka A, Wojtasiewicz K, Leniewski A, Maurin J K., Czarnocki Z, Drabowicz J, Tetrahedron: Asymmetry 2007 18 406
12. Allin S M., Gaskell S N., Towler J M. R., Page P C. B., Saha B, McKenzie W P., Martin M J., J. Org. Chem. 2007 72 8972
13. Kanemitsu T, Yamashita Y, Nagata K, Itoh T, Heterocycles 2007 74 199
14. Hou G.-H, Xie J.-H, Yan P.-C, Zhou Q.-L, J. Am. Chem. Soc. 2009 131 1366
15. Kapat A, Kumar P S., Baskaran S, Beilstein J. Org. Chem. 2007 3 No. 49; DOI: 10.1186/1860-5397-3-49
16. Kumar P S., Kapat A, Baskaran S, Tetrahedron Lett. 2008 49 1241
17. Saber M, Comesse S, Dalla V, Daïch A, Sanselme M, Netchitaïlo P, Synlett 2010 2197
18. Gilchrist T L., Chem. Soc. Rev. 1983 12 53
19. Gilchrist T L., Wood J E., In Comprehensive Heterocyclic Chemistry II Vol. 6 Boulton A J. Pergamon Press Oxford 1996 279-299
20. Tietze L F., Kettschau G, Top. Curr. Chem. 1997 189 1
21. Tsoungas P G., Heterocycles 2002 57 1149
22. Reissig H.-U, Zimmer R, In Science of Synthesis, Houben-Weyl Methods of Molecular Transformations Vol. 33 Molander G A. Georg Thieme Stuttgart 2007 371-379
23. Lemos A, Molecules 2009 14 4098
24. Gilchrist T L., Roberts T G., J. Chem. Soc., Perkin Trans. 1 1983 1283
25. Gilchrist T L., Lemos A, J. Chem. Soc., Perkin Trans. 1 1993 1391
26. Gallos J K., Sarli V C., Koftis T V., Coutouli-Argyropoulou E, Tetrahedron Lett. 2000 41 4819
27. Gallos J K., Sarli V C., Stathakis C I., Koftis T V., Nachmia V R., Coutouli-Argyropoulou E, Tetrahedron 2002 58 9351
28. Gallos J K., Sarli V C., Varvogli A C., Papadoyanni C Z., Papaspyrou S D., Argyropoulos N G., Tetrahedron Lett. 2003 44 3905
29. Gallos J K., Sarli V C., Massen Z S., Varvogli A C., Papadoyanni C Z., Papaspyrou S D., Argyropoulos N G., Tetrahedron 2005 61 565
30. Gallos J K., Alexandraki E S., Stathakis C I., Heterocycles 2007 71 1127
31. Zimmer R, Arnold T, Homann K, Reissig H.-U, Synthesis 1994 1050
32. Beugelmans R, Bois-Choussy M, Tetrahedron 1992 48 8285
33. Catsoulacos P, J. Pharm. Sci. 1976 65 625
34. Denmark S E., Cramer C J., Dappen M S., J. Org. Chem. 1987 52 87
35. Shatzmiller S, Dolitzky B.-Z, Meirovich R, Neidlein R, Weik C, Liebigs Ann. Chem. 1991 161
36. Lee I.-Y C., Lee J H., Lee H W., Bull. Korean Chem. Soc. 2002 23 537
37. Smirnov V O., Sidorenkov A S., Khomutova Y A., Ioffe S L., Tartakovsky V A., Eur. J. Org. Chem. 2009 3066
38. Reissig H.-U, Angew. Chem., Int. Ed. Engl. 1992 31 288
39. Arnold T, Orschel B, Reissig H.-U, Angew. Chem., Int. Ed. Engl. 1992 31 1033
40. Boa A N., Dawkins D A., Hergueta A R., Jenkins P R., J. Chem. Soc., Perkin Trans. 1 1994 953