T3P-Promoted, Mild, One-Pot Syntheses of Constrained Polycyclic Lactam Dipeptide Analogues via Stereoselective Pictet–Spengler and Meyers Lactamization Reactions

A new convenient, mild, one-pot procedure is described for the diastereoselective synthesis of constrained 7,5- and 7,6-fused azabicycloalkanes. Using 2-formyl-L-tryptophan and 2-formyl-l-phenylalanine as bielectrophilic building blocks, T3P-mediated Pictet–Spengler and Meyers lactamization reaction...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 18; pp. 4482 - 4485
Main Authors Jida, Mouhamad, Van der Poorten, Olivier, Guillemyn, Karel, Urbanczyk-Lipkowska, Zofia, Tourwé, Dirk, Ballet, Steven
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.09.2015
Amer Chemical Soc
Subjects
Anhydrides - chemistry
Chemistry
Chemistry, Organic
Dipeptides - chemical synthesis
Dipeptides - chemistry
Lactams - chemical synthesis
Lactams - chemistry
Models, Molecular
Molecular Conformation
Molecular Structure
Organophosphonates - chemistry
Phenylalanine
Physical Sciences
Science & Technology
Stereoisomerism
ROUTE
DESIGN
METHODOLOGY
MIMETICS
BICYCLIC LACTAMS
AMINO-ACIDS
PEPTIDOMIMETIC SYNTHESIS
SCAFFOLDS
PRO
METATHESIS
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Summary:A new convenient, mild, one-pot procedure is described for the diastereoselective synthesis of constrained 7,5- and 7,6-fused azabicycloalkanes. Using 2-formyl-L-tryptophan and 2-formyl-l-phenylalanine as bielectrophilic building blocks, T3P-mediated Pictet–Spengler and Meyers lactamization reactions were developed to present chiral and polycyclic aminoindolo- and aminobenzazepinone compounds in excellent yields. The conformationally constrained compounds can serve as templates for peptidomimetic research or polyheterocyclic privileged scaffolds.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b02145