Synthesis of benzofuranones related to diazonamide via an intramolecular pummerer reaction

Tetrahedron Letters

Volumn 40, Issue 3, 1999, Pages 451-454

  Magnus, Philip ^a   Kreisberg, Jennifer D ^a  

^a The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 THIOMETHYLBENZOFURAN 2 ONE DERIVATIVE; ALKALOID; BENZOFURAN DERIVATIVE; DIAZONAMIDE; DIAZONIUM COMPOUND; FURANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLON CARCINOMA; EXTRACTION; MELANOMA CELL; SYNTHESIS;

EID: 0033555801     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02386-7     Document Type: Article

References (25)

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15. For clarity we have chosen to designate the rings of the diazonamides as A,B etc.
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23. For a recent review of the Pummerer reaction see:- Padwa, A.; Gunn, Jr. D. E.; Osterhout, M. H. Synthesis 1997, 1353. Applications of the Pummerer reaction in the synthesis of indole alkaloids. Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
24. For a recent review of the Pummerer reaction see:- Padwa, A.; Gunn, Jr. D. E.; Osterhout, M. H.Synthesis 1997, 1353. Applications of the Pummerer reaction in the synthesis of indole alkaloids. Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
25. The esters 7 (87%), 10 (92%), 12 (75%), 18 (85%) and 20 (90%) were synthesized by DCC mediated coupling of the corresponding phenols and acids. Whereas, esters 14 (67%), 16 (86%) and 22 (67%) were synthesized using EDC as the coupling reagent.