The Journal of organic chemistry

Stereoselective Synthesis of Tilivalline1

T Nagasaka, Y Koseki

Index: Nagasaka, Tatsuo; Koseki, Yuji Journal of Organic Chemistry, 1998 , vol. 63, # 20 p. 6797 - 6801

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Citation Number: 37

Abstract

Tilivalline 1, a metabolite from Klebsiella pneumoniae var. ocytoca, was easily synthesized in five steps from (S)-proline and 3-(benzyloxy) isatoic anhydride 4 g. This synthesis is based on modified Curtius reactions of 3-substituted phthalic anhydrides 11 to 3-substituted isatoic anhydrides 4, conversion of lactams 6 to the acyliminium precursors 7 and stereoselective introduction of indole from the less hindered side of 7.