Converting Cycloalkanones into N‑Heterocycles: Formal Synthesis of (−)-Gephyrotoxin 287C
The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a...
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Published in | Journal of organic chemistry Vol. 78; no. 24; pp. 12532 - 12544 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
20.12.2013
Amer Chemical Soc |
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Abstract | The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a stereospecific manner. To showcase the method, we performed an efficient formal synthesis of (−)-gephyrotoxin 287C. |
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AbstractList | The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a stereospecific manner. To showcase the method, we performed an efficient formal synthesis of (-)-gephyrotoxin 287C. The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When coupled with the Beckmann rearrangement, this photochemical ring contraction converts cycloalkanones into N-heterocycles in a few steps and in a stereospecific manner. To showcase the method, we performed an efficient formal synthesis of (−)-gephyrotoxin 287C. |
Author | Winter, Dana K Lessard, Jean Spino, Claude Pichette, Simon |
AuthorAffiliation | Département de Chimie Université de Sherbrooke |
AuthorAffiliation_xml | – name: Université de Sherbrooke – name: Département de Chimie |
Author_xml | – sequence: 1 givenname: Simon surname: Pichette fullname: Pichette, Simon – sequence: 2 givenname: Dana K surname: Winter fullname: Winter, Dana K – sequence: 3 givenname: Jean surname: Lessard fullname: Lessard, Jean – sequence: 4 givenname: Claude surname: Spino fullname: Spino, Claude email: Claude.Spino@USherbrooke.ca |
BackLink | https://www.ncbi.nlm.nih.gov/pubmed/24188015$$D View this record in MEDLINE/PubMed |
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Keywords | THERMOLYSIS ACID ENANTIOSELECTIVE SYNTHESIS NEOTROPICAL FROG SCHMIDT REACTION ALKYLATION RING-CONTRACTION CHLOROLACTAMS ASYMMETRIC SYNTHESES THIAZOLINES |
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Snippet | The photochemical rearrangement of N-activated lactams enables their ring contraction concomitant with the migration of a carbon onto a nitrogen atom. When... |
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SubjectTerms | Alkaloids - chemical synthesis Alkaloids - chemistry Chemistry Chemistry, Organic Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Ketones - chemistry Molecular Structure Physical Sciences Science & Technology |
Title | Converting Cycloalkanones into N‑Heterocycles: Formal Synthesis of (−)-Gephyrotoxin 287C |
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