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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Divergent syntheses of okaramines C, J, L, and S-U
Xiao-Wan Li1, Tong-Xu Si2, Ya-Ping Liu2
1School of Pharmaceutical Science, Shenzhen Technology University, Shenzhen 518118, China. mzwang2000@163.com and School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou 510006, People's Republic of China.
Abstract:
The total synthesis of six novel okaramines (C, J, L, and S-U) was accomplished with a precise synthesis scheme involving a few steps and a practical yield of 6.7%-23% was obtained. The significance of this study includes the design of a successful and convenient synthesis method for preparation of 3a-hydroxy-pyrrolo[2,3-b]-indole and C-7 prenylated l-tryptophan derivatives using a nucleophilic attack of cyclopropylazetoindoline and an aza-Claisen rearrangement of N-reverse-prenyl tryptophan, respectively.
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