Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-beta-yohimbine from secologanin: a route to normal and pseudo stereoisomers of yohimbine

Authors
Brown, RT Pratt, SB Richards, P
Citation
Rt. Brown et al., Enantiospecific synthesis of (-)-3-iso-19,20-dehydro-beta-yohimbine from secologanin: a route to normal and pseudo stereoisomers of yohimbine, TETRAHEDR L, 41(30), 2000, pp. 5627-5630
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
30
Year of publication
2000
Pages
5627 - 5630
Database
ISI
SICI code
0040-4039(20000722)41:30<5627:ESO(FS>2.0.ZU;2-Q
Abstract
Hydrolysis of secologanin ethylene acetal at pH 7 resulted in stereoselecti ve aldol cyclisation to a cyclohexene aldehyde, which, on reductive aminati on and cyclisation with tryptamine afforded (-)-3-iso-19,20-dehydro-beta-yo himbine, converted into various normal and pseudo isomers of yohimbine. (C) 2000 Elsevier Science Ltd. All rights reserved.