The Journal of Organic Chemistry

Synthesis of 2-substituted. DELTA. 3-piperidines: the nitrogen analog of the Ferrier rearrangement. An approach to streptazolin

AP Kozikowski, PU Park

Index: Kozikowski, Alan P.; Park, Pyeong-uk Journal of Organic Chemistry, 1984 , vol. 49, # 9 p. 1674 - 1676

Full Text: HTML

Citation Number: 39

Abstract

1-4"" provides efficient regiocontrolled routes to a variety of differentially protected resorcinol and phloroglucinol derivatives. The synthesis of the antifungal antibiotics DB-2073 (26)15 and grifolin (27)16 demonstrates the utility ... HO 26 HO UCH , 27 of this approach. Thus, exposure of 17 to 4 equiv of tri- methylsilyl iodide" in acetonitrile (reflux, 24 h) produced DB-2073 in 89% yield, while cleavage of the methyl ether in annulation product 20 was achieved by ...