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Clerici F, Gelmi ML, Pocar D. A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids. J Org Chem. 1999;64(3):726-730doi: 10.1021/jo9810011.
Clerici, F., Gelmi, M. L., & Pocar, D. (1999). A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids. The Journal of organic chemistry, 64(3), 726-730. https://doi.org/10.1021/jo9810011
Clerici, F., et al. "A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids." The Journal of organic chemistry vol. 64,3 (1999): 726-730. doi: https://doi.org/10.1021/jo9810011
Clerici F, Gelmi ML, Pocar D. A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids. J Org Chem. 1999 Feb 05;64(3):726-730. doi: 10.1021/jo9810011. PMID: 11674139.
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J Org Chem. 1999 Feb 05;64(3):726-730. doi: 10.1021/jo9810011.

A Novel Class of Conformationally Constrained, Masked Cysteines: Synthesis of 2-Alkyl- and 2-Arylsulfanyl-1-aminocyclopropanecarboxylic Acids.

The Journal of organic chemistry

F. Clerici, M. L. Gelmi, D. Pocar

Affiliations

  1. Istituto di Chimica Organica, Facoltà di Farmacia, Università di Milano, Via Venezian 21, I-20133 Milano, Italy.

PMID: 11674139 DOI: 10.1021/jo9810011

Abstract

A convenient synthesis of 4-sulfanylmethylene-5(4H)-oxazolones 3 was realized starting from 4-(chloromethylene)oxazolone 1 and mercaptans 2. Oxazolones 3 were used as starting materials for the preparation of unknown 2-sulfanyl-1-aminocyclopropanecarboxylic acid derivatives 5 and7. Oxazolones 3 were cyclopropanated at the exocyclic double bond with diazomethane, giving a mixture of the two (Z)- and (E)-spirocyclopropane oxazolones 4 with good diastereoselectivity. These were then treated with ethanol and DMAP to produce the corresponding carboxylates 5. The trityl derivative 5d was converted into a mixture of diastereoisomeric disulfides 6 using iodine in ethanol solution. Disulfides 6 are convenient synthons for the preparation of 3-sulfanyl-substituted 2,3-methanoamino acids 7.

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