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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| CitedBy_id | crossref_primary_10_1021_jacs_5b10440 crossref_primary_10_5059_yukigoseikyokaishi_74_599 crossref_primary_10_1002_adsc_201500378 crossref_primary_10_1016_j_tet_2017_03_073 crossref_primary_10_1021_acs_orglett_1c03924 crossref_primary_10_1021_jacs_8b00136 crossref_primary_10_1021_acsomega_8b01038 crossref_primary_10_1039_D1RA04181A crossref_primary_10_1016_j_tet_2018_05_053 crossref_primary_10_3987_COM_18_S_F_43 crossref_primary_10_3987_COM_19_14171 crossref_primary_10_1002_anie_201812647 crossref_primary_10_1002_ange_201812647 crossref_primary_10_1002_ange_201409038 crossref_primary_10_1002_anie_201409038 crossref_primary_10_1016_j_tet_2017_11_045 crossref_primary_10_1246_bcsj_20140398 crossref_primary_10_1021_acs_orglett_7b03381 crossref_primary_10_1002_chin_201423178 crossref_primary_10_1021_acs_chemrev_5b00154 |
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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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