Tosylates in palladium-catalysed coupling reactions. Application to the synthesis of arylcoumarin inhibitors of gyrase B

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1543-1547

  Schio, Laurent ^a   Chatreaux, Fabienne ^a   Klich, Michel ^a  

^a SANOFI   (France)

Author keywords

Antibacterials; Coumarin; Organotin reagents; Palladium catalyst; Sulfonyl compounds

Indexed keywords

ANTIINFECTIVE AGENT; CLOROBIOCIN; COUMARIN DERIVATIVE; GYRASE INHIBITOR; NOVOBIOCIN; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0034603348     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02351-5     Document Type: Article

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18. To be published elsewhere.
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20. 3P/DEAD) were necessary for reaction completion. Consequently, laborious purification steps were required to isolate the desired α-glycoside from complex crude mixtures. For example, pure 17 was obtained after several triturating manipulations in dichloromethane and ether.
21. From 17, the coupling reaction with 5c realised in the same experimental conditions occurred in 34% yield.
22. +, 15), 268 (53), 254 (35), 108 (100).