Postcondensation modifications of ugi four-component condensation products: 1-isocyanocyclohexene as a convertible isocyanide. Mechanism of conversion, synthesis of diverse structures, and demonstration of resin capture

Journal of the American Chemical Society

Volumn 118, Issue 11, 1996, Pages 2574-2583

  Keating, Thomas A ^a   Armstrong, Robert W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BENZODIAZEPINE DERIVATIVE; CYCLOHEXENE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029963887     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953868b     Document Type: Article

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46. In a linear strategy, bifunctional or bireactive inputs are required at each step in order to provide reactive sites for succeeding steps. On the other hand, an MCC can proceed successfully with monofunctional and monoreactive inputs. This concept is illustrated by comparison of peptide synthesis with the Ugi 4CC, Each amino acid input for linear peptide synthesis incorporates two orthogonally reactive sites - one to couple to the existing peptide and the other to provide a site for further attachment However, the four inputs for the Ugi reaction all require only one reactive site. Thus, the 4CC reaction can employ a greater number and variety of inputs than can a linear strategy