An expedient strategy for the diversity-oriented synthesis of macrocyclic compounds with natural product-like characteristics

Tetrahedron

Volumn 72, Issue 25, 2016, Pages 3567-3578

  Ciardiello, Joe J ^a   Galloway, Warren R J D ^a   O'Connor, Cornelius J ^a   Sore, Hannah F ^a   Stokes, Jamie E ^a   Wu, Yuteng ^a   Spring, David R ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

Chemical space; Diversity oriented synthesis; Macrocycles; Scaffold

Indexed keywords

ANTIBIOTIC AGENT; CARBONYL DERIVATIVE; MACROCYCLIC COMPOUND; MOLECULAR SCAFFOLD; NATURAL PRODUCT;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG DEVELOPMENT; DRUG SYNTHESIS; HYDROGEN BOND; PRIORITY JOURNAL;

EID: 84964957455     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.10.061     Document Type: Article

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43. 39 Preliminary studies indicated that alkylation of the hydroxyl group in the presence of a free acid group was somewhat capricious. Therefore, when carrying out the full synthesis, it was decided to mask the acid group as an ester prior to alkylation. In addition, preliminary studies had demonstrated that azido-tosylate 38 was prone to elimination rather than substitution when reacted with compound 40. It was ascertained that replacing the tosylate group with a bromide (compound 24) greatly encouraged the desired substitution reaction and minimised the risk of elimination occurring.
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