Solid-phase synthesis of bicyclic dipeptide mimetics by intramolecular cyclization of alcohols, thiols, amines, and amides with N-acyliminium intermediates

Organic Letters

Volumn 7, Issue 17, 2005, Pages 3601-3604

  Nielsen, Thomas E ^a   Le Quement, Sebastian ^a   Meldal, Morten ^a  

^a CARLSBERG LABORATORY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMINE; DIPEPTIDE; THIOL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; AMIDES; AMINES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; DIPEPTIDES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 24044449622     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050871j     Document Type: Article

References (37)

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33. 3CN. The resulting solution was filtered through a Teflon filter and analyzed by RP-HPLC and ESMS. When cleaved from the resin with 0.1 M NaOH (aq) and neutralized with 0.1 M HCl (aq), the crude compound (4, 15a-f) was obtained as a mixture with solid NaCl. Corrected for the salt contents, crude yields were typically around 70-90%. When purified by preparative RP-HPLC, the yield of desalted, purified products generally dropped to 45-85% (consult Supporting Information).
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