Synthesis of novel 13α-18-nor-16-carboxamido steroids via a palladium-catalyzed aminocarbonylation reaction

Eszter Szánti-Pintér, Zsolt Csók, Z. Berente, L. Kollár, R. Skoda-Földes

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

13α-18-nor-16-Carboxamido steroids were synthesized via a palladium-catalyzed aminocarbonylation reaction of the corresponding iodoalkenes. The starting material was an unnatural 13α-16-keto steroid, obtained by a Wagner-Meerwein rearrangement of a 16α,17α-epoxide in the presence of [BMIM][BF4]. The 13α-16-keto steroid was converted to a mixture of 16-iodo-16-ene and 16-iodo-15-ene derivatives in two steps by Barton's methodology. Aminocarbonylation of the steroidal alkenyl iodides was carried out using different primary and secondary amines as nucleophiles. The products, 16-carboxamido-16-ene and 16-carboxamido-15-ene derivatives, were obtained in good yields and were characterized by 1H and 13C NMR, IR and MS. The reduction of the above two unsaturated carboxamides resulted in the same product, 17α-methyl- 16α-carboxamido-androstane.

Original languageEnglish
Pages (from-to)1177-1182
Number of pages6
JournalSteroids
Volume78
Issue number12-13
DOIs
Publication statusPublished - 2013

Fingerprint

Palladium
Steroids
Derivatives
Nucleophiles
Epoxy Compounds
Iodides
Amines
Nuclear magnetic resonance

Keywords

  • 13α-18-nor-Steroid
  • Aminocarbonylation
  • Iodoalkene
  • Palladium

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Endocrinology
  • Molecular Biology
  • Organic Chemistry
  • Pharmacology

Cite this

Synthesis of novel 13α-18-nor-16-carboxamido steroids via a palladium-catalyzed aminocarbonylation reaction. / Szánti-Pintér, Eszter; Csók, Zsolt; Berente, Z.; Kollár, L.; Skoda-Földes, R.

In: Steroids, Vol. 78, No. 12-13, 2013, p. 1177-1182.

Research output: Contribution to journalArticle

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AU - Berente, Z.

AU - Kollár, L.

AU - Skoda-Földes, R.

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N2 - 13α-18-nor-16-Carboxamido steroids were synthesized via a palladium-catalyzed aminocarbonylation reaction of the corresponding iodoalkenes. The starting material was an unnatural 13α-16-keto steroid, obtained by a Wagner-Meerwein rearrangement of a 16α,17α-epoxide in the presence of [BMIM][BF4]. The 13α-16-keto steroid was converted to a mixture of 16-iodo-16-ene and 16-iodo-15-ene derivatives in two steps by Barton's methodology. Aminocarbonylation of the steroidal alkenyl iodides was carried out using different primary and secondary amines as nucleophiles. The products, 16-carboxamido-16-ene and 16-carboxamido-15-ene derivatives, were obtained in good yields and were characterized by 1H and 13C NMR, IR and MS. The reduction of the above two unsaturated carboxamides resulted in the same product, 17α-methyl- 16α-carboxamido-androstane.

AB - 13α-18-nor-16-Carboxamido steroids were synthesized via a palladium-catalyzed aminocarbonylation reaction of the corresponding iodoalkenes. The starting material was an unnatural 13α-16-keto steroid, obtained by a Wagner-Meerwein rearrangement of a 16α,17α-epoxide in the presence of [BMIM][BF4]. The 13α-16-keto steroid was converted to a mixture of 16-iodo-16-ene and 16-iodo-15-ene derivatives in two steps by Barton's methodology. Aminocarbonylation of the steroidal alkenyl iodides was carried out using different primary and secondary amines as nucleophiles. The products, 16-carboxamido-16-ene and 16-carboxamido-15-ene derivatives, were obtained in good yields and were characterized by 1H and 13C NMR, IR and MS. The reduction of the above two unsaturated carboxamides resulted in the same product, 17α-methyl- 16α-carboxamido-androstane.

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