Synthetic Studies on Echinulin and Related Natural Products. II. : A Total Synthesis of Echinulin
Open Access
- 1 January 1977
- journal article
- research article
- Published by Pharmaceutical Society of Japan in YAKUGAKU ZASSHI
- Vol. 97 (5) , 558-563
- https://doi.org/10.1248/yakushi1947.97.5_558
Abstract
Total synthesis of optically active echinulin [Aspergillus eschinulatus] (14) was achieved. N,N-Bis(3,3-dimethylallyl)aniline was converted into 2,4-bis(3,3-dimethylallyl)aniline (6) in one step (23% yield) by the acid-catalyzed amino-Claisen rearrangement. The aniline (6) was transformed into 2-(1,1-dimethylallyl)-5,7-bis(3,3-dimethylallyl)gramine (11) in 5 steps (15% overall yield). The gramine (11) was condensed with diketopiperazine synthesized from L-alanine, to afford the ester. Optically active echinulin (14) was obtained from the ester in 2 steps. The overall yield of echinulin (14) from 11 was 21%.Keywords
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