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Synlett 2001; 2001(9): 1387-1390
DOI: 10.1055/s-2001-16785
DOI: 10.1055/s-2001-16785
letter
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Regioselective N-Acylation of 3-Arylmethylpiperazine-2,5-diones: Short Synthesis of (-)-Glyantrypine and (-)-Fumiquinazoline F
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Publikationsverlauf
Publikationsdatum:
28. August 2001 (online)
![](https://www.thieme-connect.de/media/synlett/200109/lookinside/thumbnails/10.1055-s-2001-16785-1.jpg)
The folded conformation of the 3-arylmethyl substituent in 2,5-bis-O-trimethylsilyl-3,6-dihydropyrazines derived from the corresponding piperazine-2,5-diones, shields the N(1)-position allowing monoacylation at the neighbouring nitrogen atom. This regioselectivity was used to develop a four-step total synthesis of (-)-glyantrypine and (-)-fumiquinazoline F starting from d-tryptophan methyl ester.
regioselectivity - acylation - Wittig reactions - asymmetric synthesis - total synthesis