Organic Chemistry

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

Authors

Abstract

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.

Content

Thumbnail image of JACS Ginkgolide synthesis final.pdf

Supplementary material

Thumbnail image of Total Synthesis of (±)-Ginkgolide C and its Congeners - SI (Final Version).pdf
Total Synthesis of Ginkgolide C and Formal Synthesis of Ginkgolides A and B
Supporting Information