Synthetic Studies on Echinulin and Related Natural Products. III. : A Total Synthesis of Neoechinulin
Open Access
- 1 January 1977
- journal article
- research article
- Published by Pharmaceutical Society of Japan in YAKUGAKU ZASSHI
- Vol. 97 (5) , 564-568
- https://doi.org/10.1248/yakushi1947.97.5_564
Abstract
Total synthesis of neoechinulin (1) [Aspergillus amstelodami] was achieved. 4-(3,3-Dimethylallyl)-2-nitroaniline (3) was synthesized from N-(3,3-dimethylallyl)-2-nitroaniline in one step (22% yield) by the acid-catalyzed amino-Claisen rearrangement. The nitroaniline (3) was converted in two steps (45% overall yield) to 5-(3,3-dimethylallyl)-2-iodoaniline, which was condensed with copper acetilide to afford 2-(1,1-dimethylallyl)-6-(3,3-dimethylallyl)-indole (6) in 94% yield. The indole (6) was synthesized in better overall yield by another route. Neoechinulin (1) was obtained from (6) in two steps (50% overall yield). Based on these results the stereochemistry of neoechinulin (1) was discussed.Keywords
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