Syntheses of differentially protected isocoumarins

Tetrahedron

Volumn 66, Issue 30, 2010, Pages 5573-5582

  Lowell, Andrew N ^a   Wall, Philip D ^a   Waters, Stephen P ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

Isocoumarin; Orthogonal protection; Rubromycin; Selective oxidation

Indexed keywords

BENZENE; CATECHOL; HALIDE; ISOCOUMARIN DERIVATIVE; POTASSIUM BICARBONATE; PURPUROMYCIN; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; HECK REACTION; HORNER WADSWORTH EMMONS REACTION; MANNICH REACTION; OLEFINATION; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 77955927135     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.05.077     Document Type: Article

References (23)

1. Waters, S. P.; Kozlowski, M. C. Tetrahedron Lett. 2001, 42, 3567-3570.
2. Brockmann, H.; Zeeck, A. Chem. Ber. 1970, 103, 1709-1726.
3. Thrash, T. P.; Welton, T. D.; Behar, V. Tetrahedron Lett. 2000, 41, 29-31.
4. Qin, D.; Ren, R. X.; Siu, T.; Zheng, C.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4709-4713.
5. Waters, S. P.; Fennie, M. W.; Kozlowski, M. C. Tetrahedron Lett. 2006, 47, 5409-5413.
6. Waters, S. P.; Fennie, M. W.;Kozlowski, M.C. Org. Lett. 2006, 8, 3243-3246.
7. Denmark, S. E.; Butler, C. R. J. Am. Chem. Soc. 2008, 130, 3690-3704.
8. Brasholz, M.; Reissig, H. U. Synlett 2004, 2736-2738.
9. Brasholz, M.; Luan, X.; Reissig, H. U. Synthesis 2005, 3571-3580.
10. Boger, D. L.; Hong, J.; Hikota, M.; Ishida, M. J. Am. Chem. Soc. 1999, 121, 2471-2477.
11. Edgar, K. J.; Falling, S. N. J. Org. Chem. 1990, 55, 5287-5291.
12. Heck, R. F. In Organic Reactions; Dauben, W. G., Ed.; John Wiley: New York, NY, 1982; Vol. 27, pp 345-390.
13. Wenkert, E.; Alonso, M. E.; Buckwalter, B. L.; Sanchez, E. L. J. Am. Chem. Soc. 1983, 105, 2021-2029.
14. Djakovitch, L.; Wagner, M.; Hartung, C. G.; Beller, M.; Koehler, K. J. Mol. Catal. 2004, 219, 121-130.
15. Barrett, A. G. M.; Barton, D. H. R.; Falck, J. R.; Papaioannou, D.; Widdowson, D. A. J. Chem. Soc., Perkin Trans. 1 1979, 652-661.
16. Morrison, C. F.; Burnell, D. J. Org. Lett. 2000, 2, 3891-3892.
17. Gagliardi, S.; Nadler, G.; Consolandi, E.; Parini, C.; Morvan, M.; Legave, M.; Belfiore, P.; Zocchetti, A.; Clarke, G. D.; James, I.; Nambi, P.; Gowen, M.; Farini, C. J. Med. Chem. 1998, 41, 1568-1573.
18. Guay, V.; Brassard, P. Synthesis 1987, 294-297.
19. Benbow, J. W.; Katoch-Rouse, R. J. Org. Chem. 2001, 66, 4965-4972.
20. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
21. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
22. Sinhababu, A. K.; Borchardt, R. T. J. Org. Chem. 1983, 48, 2356-2360.
23. Welton, T.D. Doctor of Philosophy, Rice University, 2003.