Synthesis of 1,5-benzothiazepine dipeptide mimetics via two CuI-catalyzed cross coupling reactions

Jiangang Gan; Dawei Ma

doi:10.1021/ol900943b

Synthesis of 1,5-benzothiazepine dipeptide mimetics via two CuI-catalyzed cross coupling reactions

Org Lett. 2009 Jul 2;11(13):2788-90. doi: 10.1021/ol900943b.

Authors

Jiangang Gan¹, Dawei Ma

Affiliation

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.

PMID: 19480438
DOI: 10.1021/ol900943b

Abstract

CuI-catalyzed coupling of 4-methylphenyl bromide with amino acids gives N-aryl amino acids, which are converted into linear dipeptides via iodination and condensation with L-cysteine derived acyl chloride. Cyclization is achieved via a CuI/N,N-dimethylglycine catalyzed intramolecular coupling of aryl iodides with the liberated thiol to afford 1,5-benzothiazepine dipeptide mimetics.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Copper / chemistry*
Dipeptides / chemical synthesis*
Dipeptides / chemistry
Iodides / chemistry*
Molecular Structure
Stereoisomerism
Thiazepines / chemical synthesis*
Thiazepines / chemistry

Substances

1,5-benzothiazepine
Dipeptides
Iodides
Thiazepines
Copper
cuprous iodide