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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Modular Total Synthesis of the 5/5-Spirocyclic Spiroindimicins
Ankush Banerjee1, Tiffany A Brisco1, Zhen Zhang1
1Department of Biochemistry, UT Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390, United States.
Abstract:
Total syntheses of the 5/5-spirocyclic indoline alkaloids (±)-spiroindimicins B, C, D, E, F, and G have been achieved via a modular approach. Our route features direct coupling of halogenated pyrrolemetal and isatin partners, Suzuki coupling to append the indole unit, Lewis acid-mediated spirocyclization, and divergent functionalization to give various family members. These syntheses are concise (six or seven steps from commercial materials) and highly amenable to analogue synthesis.
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