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Diastereoselective Synthesis of 1-Hydroxy-Substituted Benzo[b]quinolidines and 11-Hydroxy-Substituted Azepino[1,2-b]isoquinolines via Hetero-Ene Cyclization

✍ Scribed by Monsees, Axel ;Laschat, Sabine ;Kotila, Sirpa ;Fox, Thomas ;Würthwein, Ernst-Ulrich

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
906 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

(L)‐Phenylalanine 4 can be converted to N‐(4‐methyl‐3‐pentenyl)tetrahydrosisoquinoline‐3‐carbaldehyde 10 and the corresponding homologous aldehyde 19 in 4 and 5 steps, respectively, by employing the Pictet–Spengler reaction as the key step. After Lewis acid catalyzed cyclization of 10 and 19 the cis‐configured 1‐hydroxybenzo[b]quinolizidine 21a and 11‐hydroxyazepino[1,2‐b]isoquinoline 22a were obtained with high diastereoselectivities. Compound 21a, which was characterized by X‐ray structure analysis, displays a fishbone pattern of endless zig‐zag chains connected via intermolecular hydrogen bonds in the solid state.

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ChemInform Abstract: Diastereoselective
ChemInform Abstract: Diastereoselective Synthesis of 1-Hydroxy-Substituted Benzo(b) quinolidines and 11-Hydroxy-Substituted Azepino(1,2-b)isoquinolines via Hetero-Ene Cyclization.
✍ A. MONSEES; S. LASCHAT; S. KOTILA; T. FOX; E.-U. WUERTHWEIN 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 34 KB 👁 1 views

Diastereoselective Synthesis of 1-Hydroxy-Substituted Benzo(b) quinolidines and 11-Hydroxy-Substituted Azepino(1,2-b)isoquinolines via Hetero-Ene Cyclization. -The title compounds (VIII) and (XV) are prepared by Lewis acid-catalyzed cyclizations of (VII) and (XIV), resp., obtained from (S)-(I) by a