Total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]- isoquinolines involving free radical cyclizations induced by tributyltin(IV) hydride

Authors
Martinez, E Estevez, JC Estevez, RJ Castedo, L
Citation
E. Martinez et al., Total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[2,1-f]- isoquinolines involving free radical cyclizations induced by tributyltin(IV) hydride, TETRAHEDRON, 57(10), 2001, pp. 1973-1979
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
10
Year of publication
2001
Pages
1973 - 1979
Database
ISI
SICI code
0040-4020(20010303)57:10<1973:TSO1I>2.0.ZU;2-D
Abstract
We describe two total syntheses of 1-methyl-1,2,3,4-tetrahydronaphtho[1,2-f ]isoquinolines based on free radical cyclization. One of them includes the cyclization of N-{2-[2-(2-bromophenyl)-1-methoxyethyl]phenylethyl}acetamide s and subsequent transformation of the resulting N-[2-(10-methoxy-9, 10-dih ydro-1-phenanthryl)ethyl]acetamides. The second is based on the known cycli zation of 1-(2-bromobenzyl)isochroman-3-ones to 4,5, 6a,7-tetrahydrodibenzo [de,g]chroman-3-ones followed by transformation of the resulting 2-(1-phen anthryl)acetamides. (C) 2001 Elsevier Science Ltd. All rights reserved.