4.8 Article

A Concise Approach to a Gelsemine Core Structure using an Oxygen to Carbon Bridge Swapping Strategy

Journal

ORGANIC LETTERS
Volume 10, Issue 21, Pages 4747-4750

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801835q

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Funding

  1. EPSRC
  2. EPSRC [EP/D010233/1] Funding Source: UKRI
  3. Engineering and Physical Sciences Research Council [EP/D010233/1] Funding Source: researchfish

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A tricyclic core structure 2 related to gelsemine 1 was synthesized from an oxabicyclo[3.2.1]octanone 4 by a three-step bridge swapping strategy involving elimination of the bridging ether oxygen and intramolecular Michael addition of a tethered cyanoacetamide unit.

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