ChemInform Abstract: Converting Cycloalkanones into N-Heterocycles: Formal Synthesis of (-)-Gephyrotoxin 287C

ChemInform Abstract: Converting Cycloalkanones into N-Heterocycles: Formal Synthesis of (-)-Gephyrotoxin 287C

Key step in the synthesis of Kishi′s intermediate (VIII) on the way to the natural alkaloid gephyrotoxin 287C (IX) is the combination of Beckmann ring expansion and photochemical ring contraction to convert cyclopentanone (I) into pyrrolidine (VI) stereospecifically.

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Veröffentlicht in:ChemInform 2014-06, Vol.45 (23), p.no-no
Hauptverfasser: Pichette, Simon, Winter, Dana K., Lessard, Jean, Spino, Claude
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
chemoluminescence
photochemistry
photochemistry, radiation chemistry, chemoluminescence
pyridine derivatives with bridges
radiation chemistry
ring contraction
ring expansion
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Zusammenfassung:Key step in the synthesis of Kishi′s intermediate (VIII) on the way to the natural alkaloid gephyrotoxin 287C (IX) is the combination of Beckmann ring expansion and photochemical ring contraction to convert cyclopentanone (I) into pyrrolidine (VI) stereospecifically.
ISSN:0931-7597
1522-2667
DOI:10.1002/chin.201423178