A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives
A concise synthesis of (16<i>S</i>,20<i>S</i>)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin o...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-05-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/10/2377 |
| _version_ | 1797567468461359104 |
|---|---|
| author | Agnieszka Wojtkielewicz Damian Pawelski Przemysław Bazydło Aneta Baj Stanisław Witkowski Jacek W. Morzycki |
| author_facet | Agnieszka Wojtkielewicz Damian Pawelski Przemysław Bazydło Aneta Baj Stanisław Witkowski Jacek W. Morzycki |
| author_sort | Agnieszka Wojtkielewicz |
| collection | DOAJ |
| description | A concise synthesis of (16<i>S</i>,20<i>S</i>)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et<sub>3</sub>SiH/TFA or Et<sub>3</sub>SiH/Bi(TfO)<sub>3</sub>. Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. <i>N</i>-Alkyl derivatives were also obtained in a similar way. |
| first_indexed | 2024-03-10T19:42:24Z |
| format | Article |
| id | doaj.art-fe2851da240e46f0b6c87cf95e2805df |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:42:24Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-fe2851da240e46f0b6c87cf95e2805df2023-11-20T01:09:40ZengMDPI AGMolecules1420-30492020-05-012510237710.3390/molecules25102377A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl DerivativesAgnieszka Wojtkielewicz0Damian Pawelski1Przemysław Bazydło2Aneta Baj3Stanisław Witkowski4Jacek W. Morzycki5Faculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, PolandFaculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, PolandFaculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, PolandFaculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, PolandFaculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, PolandFaculty of Chemistry, University of Białystok, K. Ciołkowskiego 1K, 15-245 Białystok, PolandA concise synthesis of (16<i>S</i>,20<i>S</i>)-3β-hydroxy-5α-pregnane-20,16-carbolactam from tigogenin via the corresponding lactone is described. The most efficient synthetic route consisted of the lactone ring-opening with aminoalane reagent followed by PDC or Dess-Martin oxidation. The oxo-amide obtained was subjected to cyclization with Et<sub>3</sub>SiH/TFA or Et<sub>3</sub>SiH/Bi(TfO)<sub>3</sub>. Alternately, the lactone was converted first to the oxo-acid, which was then subjected to the microwave-assisted reductive amination. <i>N</i>-Alkyl derivatives were also obtained in a similar way.https://www.mdpi.com/1420-3049/25/10/2377lactamsreductive aminationspirostane degradationsteroids |
| spellingShingle | Agnieszka Wojtkielewicz Damian Pawelski Przemysław Bazydło Aneta Baj Stanisław Witkowski Jacek W. Morzycki A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives Molecules lactams reductive amination spirostane degradation steroids |
| title | A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives |
| title_full | A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives |
| title_fullStr | A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives |
| title_full_unstemmed | A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives |
| title_short | A Convenient Synthesis of (16<i>S</i>,20<i>S</i>)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its <i>N</i>-alkyl Derivatives |
| title_sort | convenient synthesis of 16 i s i 20 i s i 3β hydroxy 5α pregnane 20 16 carbolactam and its i n i alkyl derivatives |
| topic | lactams reductive amination spirostane degradation steroids |
| url | https://www.mdpi.com/1420-3049/25/10/2377 |
| work_keys_str_mv | AT agnieszkawojtkielewicz aconvenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT damianpawelski aconvenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT przemysławbazydło aconvenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT anetabaj aconvenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT stanisławwitkowski aconvenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT jacekwmorzycki aconvenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT agnieszkawojtkielewicz convenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT damianpawelski convenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT przemysławbazydło convenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT anetabaj convenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT stanisławwitkowski convenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives AT jacekwmorzycki convenientsynthesisof16isi20isi3bhydroxy5apregnane2016carbolactamanditsinialkylderivatives |