The Journal of Organic Chemistry

Generation and reactions of the dianion of 3-hydroxy-5-methylisoxazole, a convenient. beta.-oxo amide synthon. Total synthesis of muscimol

TA Oster, TM Harris

Index: Oster, Timothy A.; Harris, Thomas M. Journal of Organic Chemistry, 1983 , vol. 48, # 23 p. 4307 - 4311

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Citation Number: 38

Abstract

The title compound (4) has been prepared by treatment of diketene with N, O-bis (trimethylsily1) hydroxylamine (2) to give N-(trimethylsiloxy)-N-(trimethylsilyl) acetoacetamide (3) as a stable liquid. Treatment of 3 with methanolic HCl removed the Me3Si protective groups and cyclized the resulting hydroxamic acid to isoxazole 4 in good yield. The dianion of 4 was generated with lithium diisopropylamide and was found to ...