Tetrahedron

Total synthesis of (±)-camphorataimides and (±)-himanimides by NaBH 4/Ni (OAc) 2 or Zn/AcOH stereoselective reduction

CF Cheng, ZC Lai, YJ Lee

Index: Cheng, Chia-Fu; Lai, Zhen-Chang; Lee, Yean-Jang Tetrahedron, 2008 , vol. 64, # 19 p. 4347 - 4353

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Citation Number: 24

Abstract

Maleic anhydride 1 of Antrodia camphorate, which can be isolated from Chinese herbal medicine, is achieved in which the longest linear sequence is only five steps, in 40% overall yield from commercially available succinic anhydride. The crucial antrodimides 3 and 2 can be readily transformed by the chemoselective reduction with Zn/AcOH and NaBH4/Ni (OAc) 2· 4H2O to afford the naturally occurring camphorataimides, 4 and 5, in high yields as well ...