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Synthetic and stereochemical studies on phthalideisoquinoline hemiacetals

✍ Scribed by Rozwadowska, Maria D. ;Matecka, Dorota

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
349 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The two new phthalideisoquinoline hemiacetals rac‐egenine (3) and rac‐corytensine (4) are prepared by stereoselective DIBAL reduction of rac‐bicuculline (1) and rac‐adlumidine (2), respectively. The identity of egenine (3) with decumbensine as well as of corytensine (4) with epi‐α‐decumbensine and humosine A is postulated. The configuration around the anomeric center in natural (+)‐egenine (3), (+)‐corytensine (4) and (−)‐narcotine hemiacetal (7) is deduced as (7′S), (7′R) and (7′R), respectively.

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