Model Experiments on Surugatoxin Synthesis. V. Construction of the Dehydrated Surugatoxin Ring System (2)

Model Experiments on Surugatoxin Synthesis. V. Construction of the Dehydrated Surugatoxin Ring System (2)

The dehydrated surugatoxin framework was constructed by the following reactions. Oxidative acetylation of tetrahydropteridine 2 with Ac2O-pyridine to dihydropteridinediacetate 5, followed by reduction (NaBH3CN), gave a isatinylidene derivative 8. Acylation of 8 with pyruvoyl chloride in benzene gave...

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Veröffentlicht in:YAKUGAKU ZASSHI 1985/04/25, Vol.105(4), pp.375-380
Hauptverfasser: OKADA, KUNISUKE, HASHIZUME, KIYOMATSU, KAKOI, HISAE, TANINO, HIDEO, INOUE, SHOJI
Format: Artikel
Sprache:eng
Schlagworte:
dihydropteridine derivative
oxidative acetylation
pentacyclic framework
selective reduction
stereospecific ring closure
surugatoxin
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Zusammenfassung:The dehydrated surugatoxin framework was constructed by the following reactions. Oxidative acetylation of tetrahydropteridine 2 with Ac2O-pyridine to dihydropteridinediacetate 5, followed by reduction (NaBH3CN), gave a isatinylidene derivative 8. Acylation of 8 with pyruvoyl chloride in benzene gave pyruvoyl amide 9. Heating 9 in pyridine at 50°C resulted in a stereospecific ring closure to afford ethyl ester analogue 10 of dehydrated surugatoxin.
ISSN:0031-6903
1347-5231
DOI:10.1248/yakushi1947.105.4_375