Convenient synthesis of cyclohexa[a]pyrrolo[2,1-b][3]benzazepine, a cephalotaxus alkaloid analogue

Authors
Tanaka, H Doi, M Shimizu, H Etoh, H
Citation
H. Tanaka et al., Convenient synthesis of cyclohexa[a]pyrrolo[2,1-b][3]benzazepine, a cephalotaxus alkaloid analogue, HETEROCYCLE, 51(10), 1999, pp. 2415-2421
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
10
Year of publication
1999
Pages
2415 - 2421
Database
ISI
SICI code
0385-5414(19991001)51:10<2415:CSOCAC>2.0.ZU;2-X
Abstract
Irradiation of N-(3-hydroxy-4-methoxyphenethyl) -3-(2-iodo-5-methoxyphenyl) propionamide (11) in methanol in the presence of sodium hydroxide furnished 3-hydroxy-2,12-dimethoxy-6,7,9,10-tetrahydrodibenz[d3]azecin-8(5H)-one (14 ) which was successfully led to cephalotaxine analogue (17) bearing pyrrolo [2,1-b][3]benzazepine skeleton by reduction with borane followed by Birch r eduction and subsequent acidic treatment. The structure of 17 was establish ed by means of X-Ray crystallography.