Palladium catalyzed cross-coupling acylation approach to the antitumor antibiotic Fredericamycin A

Tetrahedron Letters

Volumn 37, Issue 9, 1996, Pages 1367-1370

  Evans, P Andrew ^a   Brandt, Thomas A ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FREDERICAMYCIN A;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029926714     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00055-X     Document Type: Article

References (31)

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2. 5f
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28. 6e Treatment of the carboxylic acid 12 with oxalyl chloride and a catalytic amount of dimethylformamide furnished the acid chloride 8 in 97% yield. Scheme 2 Equation resented.
29. 13C NMR) and analytical (HRMS) data in accord with the assigned structure.
30. Commercial zinc chloride in diethyl ether was found to be significantly inferior in this reaction.
31. 4, filtered and the solvent removed in vacuo to afford a crude oil. Purification by flash chromatography on silica gel (eluting with ethyl acetate/hexane 1: 4) furnished 9 (1.174 g, 72%) as a pale yellow colored solid; mp 75-78 °C.