Toward the total synthesis of phorboxazole A: Synthesis of an advanced C4-C32 subunit using the Jacobsen hetero Diels-Alder reaction

Tetrahedron Letters

Volumn 44, Issue 19, 2003, Pages 3749-3754

  Paterson, Ian ^a   Luckhurst, Chris A ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE DERIVATIVE; CHROMIUM; KETONE DERIVATIVE; OXAZOLE DERIVATIVE; PHORBOXAZOLE A; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHIRALITY; DIELS ALDER REACTION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; JACOBSEN HETERO DIELS ALDER REACTION; METHODOLOGY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BETULACEAE;

EID: 0037420763     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00754-8     Document Type: Article

References (44)

1. Searle P.A., Molinski T.F. J. Am. Chem. Soc. 117:1995;8126.
2. Searle P.A., Molinski T.F., Brzezinski L.J., Leahy J.W. J. Am. Chem. Soc. 118:1996;9422.
3. Molinski T.F. Tetrahedron Lett. 37:1996;7879.
4. Forsyth C.J., Ahmed F., Cink R.D., Lee C.S. J. Am. Chem. Soc. 120:1998;5597.
5. Ahmed F., Forsyth C.J. Tetrahedron Lett. 39:1998;183.
6. Cink R.D., Forsyth C.J. J. Org. Chem. 62:1997;5672.
7. Lee C.S., Forsyth C.J. Tetrahedron Lett. 37:1996;6449.
8. Evans D.A., Fitch D.M., Smith T.E., Cee V.J. J. Am. Chem. Soc. 122:2000;10033.
9. Evans D.A., Cee V.J., Smith T.E., Fitch D.M., Cho P.S. Angew. Chem., Int. Ed. Engl. 39:2000;2533.
10. Smith A.B. III, Minbiole K.P., Verhoest P.R., Schelhaas M. J. Am. Chem. Soc. 123:2001;10942.
11. Smith A.B. III, Verhoest P.R., Minbiole K.P., Lim J.J. Org. Lett. 1:1999;909.
12. Smith A.B. III, Minbiole K.P., Verhoest P.R., Beauchamp T.J. Org. Lett. 1:1999;913.
13. Williams D.R., Clark M.P. Tetrahedron Lett. 40:1999;2291.
14. Williams D.R., Clark M.P., Berliner M.A. Tetrahedron Lett. 40:1999;2287.
15. Williams D.R., Clark M.P., Emde U., Berliner M.A. Org. Lett. 2:2000;3023.
16. Rychnovsky S.D., Thomas C.R. Org. Lett. 2:2000;1217.
17. Schaus J.V., Panek J.S. Org. Lett. 2:2000;469.
18. Huang H., Panek J.S. Org. Lett. 3:2001;1693.
19. Wolbers P., Hoffmann H.M.R. Tetrahedron. 55:1999;1905.
20. Wolbers P., Misske A.M., Hoffmann H.M.R. Tetrahedron Lett. 40:1999;4527.
21. Ye T., Pattenden G. Tetrahedron Lett. 39:1998;319.
22. Pattenden G., Plowright A.T., Tornos J.A., Ye T. Tetrahedron Lett. 39:1998;6099.
23. Pattenden G., Plowright A.T. Tetrahedron Lett. 41:2000;983.
24. Greer P.B., Donaldson W.A. Tetrahedron. 58:2002;6009.
25. White J.D., Kranemann C.L., Kuntiyong P. Org. Lett. 3:2001;4003.
26. Paterson I., Arnott E.A. Tetrahedron Lett. 39:1998;7185.
27. Paterson I., Goodman J.M., Isaka M. Tetrahedron Lett. 30:1989;7121.
28. Paterson I., Norcross R.D., Ward R.A., Romea P., Lister M.A. J. Am. Chem. Soc. 116:1994;11287.
29. Paterson I., Nowak T. Tetrahedron Lett. 37:1996;8243.
30. for a review of boron-mediated aldol reactions, see: Cowden C.J., Paterson I. Org. React. 51:1997;1.
31. Evans D.A., Hoveyda A.H. J. Am. Chem. Soc. 112:1990;6447.
32. Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., Sakai T. Tetrahedron Lett. 25:1984;2183.
33. Nuzillard J.-M., Boumendjel A., Massiot G. Tetrahedron Lett. 30:1989;3779.
34. 11 was generated from the corresponding methyl oxazole by deprotonation with lithium diethylamide (-78°C, THF) then quenching with TMSCl: Evans D.A., Cee V.J., Smith T.E., Santiago K.J. Org. Lett. 1:1999;87.
35. De Mico A., Margarita R., Parlanti L., Vescovi A., Piancatelli G. J. Org. Chem. 62:1997;6974.
36. Dossetter A.G., Jamison T.F., Jacobsen E.N. Angew. Chem., Int. Ed. Engl. 38:1999;2398.
37. Mikami K., Matsumoto S., Ishida A., Takamuku S., Suenobu T., Fukuzumi S. J. Am. Chem. Soc. 117:1995;11134.
38. The absolute configuration was determined by Mosher ester derivatisation of the equatorial alcohol 19. This also enabled quantification of the enantiomeric excess, which was corroborated by chiral HPLC (Daicel AD column) analysis of 17 and comparison with ent-17 made using the enantiomeric Jacobsen catalyst.
39. Evans D.A., Kozlowski M.C., Murry J.A., Burgey C.S., Campos K.R., Connell B.T., Staples R.J. J. Am. Chem. Soc. 121:1999;669.
40. Dahanukar V.H., Rychnovsky S.D. J. Org. Chem. 61:1996;8317.
41. Lewis M.D., Cha J.K., Kishi Y. J. Am. Chem. Soc. 104:1982;4976.
42. +) 823.4330 found 823.4324.
43. After submission of this manuscript the Pattenden and Williams groups disclosed their completed total syntheses of phorboxazole A, see: González, M. A.; Pattenden, G. Angew. Chem., Int. Ed. 2003, 42, 1255. Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Angew. Chem., Int. Ed. 2003, 42, 1258.
44. After submission of this manuscript the Pattenden and Williams groups disclosed their completed total syntheses of phorboxazole A, see: González, M. A.; Pattenden, G. Angew. Chem., Int. Ed. 2003, 42, 1255. Williams, D. R.; Kiryanov, A. A.; Emde, U.; Clark, M. P.; Berliner, M. A.; Reeves, J. T. Angew. Chem., Int. Ed. 2003, 42, 1258.