Synthesis development of an aminomethylcycline antibiotic via an electronically tuned acyliminium Friedel-Crafts reaction

Tetrahedron Letters

Volumn 49, Issue 42, 2008, Pages 6095-6100

  Chung, John Y L ^a   Hartner, Frederick W ^a   Cvetovich, Raymond J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Acyliminium; Aminomethylcycline; Back epimerization; Friedel Crafts; Minocycline

Indexed keywords

ANTIBIOTIC AGENT; CALCIUM CHLORIDE; IMINE; PTK 0796; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DECOMPOSITION; DEPROTECTION REACTION; DRUG PURIFICATION; DRUG STABILITY; DRUG SYNTHESIS; EPIMERIZATION; FRIEDEL CRAFTS REACTION; MANNICH REACTION; SUZUKI REACTION;

EID: 50649086342     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.08.011     Document Type: Article

References (28)

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28. 4 (3 g) was added and stirred at 22 °C for 1 h. The mixture was filtered, washed with hexanes (85 mL), and evaporated to dryness to afford 12.78 waxy white solid (94.7%).