Organic Chemistry

Total Synthesis of Ginkgolide C and Formal Synthesis Ginkgolides A and B



Ginkgolides are diterpenes isolated from ginkgo biloba that exhibit strong PAF antagonistic activity as well as other interesting neuroprotective properties. These natural products possess a compact, highly oxygenated hexacyclic structure with two adjacent quaternary carbon centers, an unusual tert-butyl group, and up to twelve contiguous stereogenic carbon centers. The molecular architecture of ginkgolides, coupled with their remarkable biological profile, continues to be a source of fascination but also presents a formidable challenge for chemical synthesis. Herein, we reported the first total synthesis of ginkgolide C and the formal syntheses of ginkgolides A and B. The key to achieving these syntheses is a careful orchestration of carbon-carbon bond formation, guided by the compact nature of the ginkgolide structure.


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Supplementary material

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Total Synthesis of Ginkgolide C and Formal Synthesis of Ginkgolides A and B
Supporting Information