Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid, (+/-)-erythratidine

Authors
Hosoi, S Nagao, M Tsuda, Y Isobe, K Sano, T Ohta, T
Citation
S. Hosoi et al., Synthesis of four possible stereoisomers of 1,2-epoxy-3-hydroxyerythrinans: total synthesis of an alkenoid-type erythrinan alkaloid, (+/-)-erythratidine, J CHEM S P1, 10, 2000, pp. 1505-1511
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Volume
10
Year of publication
2000
Pages
1505 - 1511
Database
ISI
SICI code
0300-922X(2000)10:<1505:SOFPSO>2.0.ZU;2-B
Abstract
Four stereoisomers of 1,2-epoxy-3-hydroxyerythrinans are synthesized and th eir stereochemistries determined unambiguously. Of these, the 1,2 alpha-epo xy-3 alpha-alcohol 4 is converted to the alkenoid-type alkaloid, (+/-)-eryt hratidine 1, utilizing reductive migration of an alpha,beta-unsaturated gam ma,delta-epoxyamide with samarium diiodide as a key step.