First total synthesis of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline annoretine

Authors
Pampin, MC Estevez, JC Castedo, L Estevez, RJ
Citation
Mc. Pampin et al., First total synthesis of the 1,2,3,4-tetrahydronaphtho[2,1-f]isoquinoline annoretine, TETRAHEDR L, 42(12), 2001, pp. 2307-2308
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
12
Year of publication
2001
Pages
2307 - 2308
Database
ISI
SICI code
0040-4039(20010318)42:12<2307:FTSOT1>2.0.ZU;2-F
Abstract
Here we describe the first total synthesis of the 1,2,3,4-tetrahydronaphtho [2,1-f]isoquinoline (6) annoretine from N-carbethoxy-o-styrylphenylethylami nes 2. The key steps were the Bischler-Napieralski reaction to form the iso quinoline unit and photocyclization of the resulting 5-styrylisoquinoline 3 to naphtoisoquinoline 4. (C) 2001 Elsevier Science Ltd. All rights reserve d.