Synthesis of the tetracyclic core of the bisabosquals

Tetrahedron Letters

Volumn 45, Issue 26, 2004, Pages 5015-5018

  Snider, Barry B ^a   Lobera, Mercedes ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

Alcohol inversion; Inverse electron demand Diels Alder reaction; Quinone methide

Indexed keywords

ALCOHOL; ALKENE; ANTIFUNGAL AGENT; BISABOSQUAL A; CARBENE; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 2942596218     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.005     Document Type: Article

References (24)

1. Minagawa K., Kouzuki S., Nomura K., Yamaguchi T., Kawamura Y., Matsushima K., Tani H., Ishii K., Tanimoto T., Kamigauchi T. J. Antibiot. 54:2001;890-895
2. Minagawa K., Kouzuki S., Nomura K., Kawamura Y., Tani H., Terui Y., Nakai H., Kamigauchi T. J. Antibiot. 54:2001;896-903
3. Mechoulam R., Ben-Shabat S. Nat. Prod. Rep. 16:1999;131-143
4. Razdan R.K. ApSimon J. The Total Synthesis of Natural Products. Vol. 4:1981;185-262 Wiley and Sons, New York
5. Van De Water R.W., Pettus T.R.R. Tetrahedron. 58:2002;5367-5405
6. Boger D.L., Weinreb S.N. Hetero Diels-Alder Methodology in Organic Synthesis. 1987;Academic, San Diego. pp 193-200
7. Snider, B. B.; Lobera, M.; Zhou, Y. unpublished results
8. Moore M., Rickards R.W., Rønneberg H. Aust. J. Chem. 37:1984;2339-2348
9. Townsend C.A., Davis S.G., Christensen S.B., Link J.C., Lewis C.P. J. Am. Chem. Soc. 103:1981;6885-6888
10. Ohta S., Nozaki A., Ohashi N., Matsukawa M., Okamoto M. Chem. Pharm. Bull. 36:1988;2239-2243
11. Hanessian S., Delorme D., Dufresne Y. Tetrahedron Lett. 25:1984;2515-2518
12. Rigby J.H., Wilson J.Z. Tetrahedron Lett. 25:1984;1429-1432
13. +) 258.1620, found 258.1612
14. Towne T.B., McDonald F.E. J. Am. Chem. Soc. 119:1997;6022-6028
15. McDonald F.E., Schultz C.C. Tetrahedron. 53:1997;16435-16448
16. González I.C., Forsyth C.J. J. Am. Chem. Soc. 122:2000;9099-9108
17. McDonald F.E., Singhi A.D. Tetrahedron Lett. 38:1997;7683-7686
18. Schlecht M., Kim H.-J. J. Org. Chem. 54:1989;583-587
19. Homsi F., Robin S., Rousseau G. Org. Synth. 77:1999;206-211
20. Uliss D.B., Razdan R.K., Dalzell H.C., Handrick G.R. Tetrahedron. 33:1977;2055-2059
21. +) 274.1569, found 274.1558
22. +) 256.1463, found 256.1471
23. 13C NMR 208.4, 160.5, 151.4, 141.1, 108.4, 103.4, 87.5, 78.5, 39.1, 38.7, 29.7, 26.7, 26.4, 22.7, 22.1 (one quaternary carbon was not observed)
24. +) 274.1569, found 274.1570