✦ LIBER ✦

Synthetic study on echinulin and related compounds. Part II. A stereoselective total synthesis of optically active echinulin

✍ Scribed by Noboru Takamatsu; Shoji Inoue; Yoshito Kishi

Publisher: Elsevier Science
Year: 1971
Tongue: French
Weight: 151 KB
Volume: 12
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)97557-4

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✦ Synopsis

In connection with investigations directed towards the total synthesis of echinulin (lo), we have reported a synthesis of 2,4-di(3,3-dimethylallyl)aniline

(1) from N,N-di(3,3-dimethylallyl)aniline by an acid-catalyzed amino Claisen rearrangement!.

In this communication, we would like to describe a stereoselective total synthesis of optically active echinulin (10) *

According to Saxtons' method: the aniline (1) was condensed with purified ethyl 4-bromo-2,2-dimethylacetoacetate to yield the isobutyrate (2)tg5 After the isobutyrate (2) was reduced to the primary alcohol (3)4 by the reduction with lithium aluminum hydride, it was oxidized to the aldehyde (4)4 with Ac20-DMSO.

The aldedhye (4) was converted to the indole (5)4,7 by Wittig reactoin, which was then transformed to the corresponding gramine (6)4'8 by Mannich reaction.

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