Formal Syntheses of (±)-Stemonamine and (±)-Cephalotaxine

Formal Syntheses of (±)-Stemonamine and (±)-Cephalotaxine

A short and efficient approach to aza-quaternary pyrrolo[1,2-a]azepine 8 and aza-quaternary indolizine 23, as the crucial intermediates for syntheses of stemonamine (1a) and cephalotaxine (1b), has been developed on the basis of the key intramolecular Schmidt reaction of symmetric azido-diones 5 and...

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Veröffentlicht in:Journal of organic chemistry 2009-04, Vol.74 (8), p.3211-3213
Hauptverfasser: Zhao, Yu-Ming, Gu, Peiming, Zhang, Hai-Jun, Zhang, Qing-Wei, Fan, Chun-An, Tu, Yong-Qiang, Zhang, Fu-Min
Format: Artikel
Sprache:eng
Schlagworte:
4-Butyrolactone - analogs & derivatives
4-Butyrolactone - chemical synthesis
4-Butyrolactone - chemistry
Azepines - chemical synthesis
Azepines - chemistry
Azides - chemistry
Catalysis
Chemistry
Exact sciences and technology
Harringtonines - chemical synthesis
Harringtonines - chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Magnetic Resonance Spectroscopy
Molecular Structure
Organic chemistry
Preparations and properties
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Zusammenfassung:A short and efficient approach to aza-quaternary pyrrolo[1,2-a]azepine 8 and aza-quaternary indolizine 23, as the crucial intermediates for syntheses of stemonamine (1a) and cephalotaxine (1b), has been developed on the basis of the key intramolecular Schmidt reaction of symmetric azido-diones 5 and 18, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo900113s