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Diastereoselective Synthesis of 1-Hydroxy-Substituted Benzo[b]quinolidines and 11-Hydroxy-Substituted Azepino[l,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
54 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis


On page 536, in place of Figure I , Scheme 5 has inadvertently been repeated; the missing Figure 1 is given below.


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Diastereoselective Synthesis of 1-Hydrox
✍ Monsees, Axel ;Laschat, Sabine ;Kotila, Sirpa ;Fox, Thomas ;Würthwein, Ernst-Ulr 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 906 KB

## 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

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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. -The title compounds (VIII) and (XV) are prepared by Lewis acid-catalyzed cyclizations of (VII) and (XIV), resp., obtained from (S)-(I) by a