Reaction of novel imide reducing reagents with pyrrolizidinediones

…, RH Rynbrandt, DC Zimmermann, LT Bell…

Index: Thomas, Edward W.; Rynbrandt, Ronald H.; Zimmermann, David C.; Bell, Larry T.; Muchmore, Christine R.; Yankee, Ernest W. Journal of Organic Chemistry, 1989 , vol. 54, # 19 p. 4535 - 4543

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Citation Number: 18

Abstract

The reduction of pyrrolizidinediones 4a and 4b with (i-Bu), AlH and LiBHEt3 affords the corresponding hexahydro-5-hydroxy-3H-py~ rolizin-3-ones 8a and 8b in good yield. LiBHEt, also reduces N-methylglutarimide (18) in 53% yield. The combination of N&H4/MeOH/Ac2O/ CH2Cl2 selectivity reduces an imide in the presence of an ester. Hexahydro-5-(methylthio)- 3H-pyrrolizin-3-ones are products of the NaBH, reduction of pyrrolizidinediones in MeSH/ ...