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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Bibliographic Details
Published inJournal of organic chemistry Vol. 78; no. 24; pp. 12532 - 12544
Main Authors Pichette, Simon, Winter, Dana K, Lessard, Jean, Spino, Claude
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.12.2013
Amer Chemical Soc
Subjects
Alkaloids - chemical synthesis
Alkaloids - chemistry
Chemistry
Chemistry, Organic
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Ketones - chemistry
Molecular Structure
Physical Sciences
Science & Technology
THERMOLYSIS
ACID
ENANTIOSELECTIVE SYNTHESIS
NEOTROPICAL FROG
SCHMIDT REACTION
ALKYLATION
RING-CONTRACTION
CHLOROLACTAMS
ASYMMETRIC SYNTHESES
THIAZOLINES
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Summary: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.
Bibliography:ObjectType-Article-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo402217e