Biomimetic Total Synthesis of the Spiroindimicin Family of Natural Products

Xikang Zheng, Yan Li, Mengtie Guan, Lingyue Wang, Shilong Wei, Yi Cheng Li, Chin Yuan Chang, Zhengren Xu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

A unified strategy for the biomimetic total synthesis of the spiroindimicin family of natural products was reported. Key transformations include a one-pot two-enzyme-catalyzed oxidative dimerization of L-tryptophan/5-chloro-L-tryptophan to afford the bis-indole precursors chromopyrrolic acid/5′,5′′-dichloro-chromopyrrolic acid, and regioselective C3′−C2′′ and C3′−C4′′ bond formation converting a common bis-indole skeleton to two skeletally different natural products, including (±)-spiroindimicins D and G with a [5,5] spiro-ring skeleton, and (±)-spiroindimicins A and H with a [5,6] spiro-ring skeleton, respectively.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
StateAccepted/In press - 2022

Keywords

  • Bioinspired Synthesis
  • Chemo-Enzymatic Synthesis
  • Natural Products
  • Spirocyclization
  • Total Synthesis

Fingerprint

Dive into the research topics of 'Biomimetic Total Synthesis of the Spiroindimicin Family of Natural Products'. Together they form a unique fingerprint.

Cite this