Advanced Synthetic Strategies toward Ginkgolide Diterpenoids: Total Synthesis of (±)-Ginkgolide C and Formal Syntheses of (±)-Ginkgolides A and B
Advanced Synthetic Strategies toward Ginkgolide Diterpenoids: Total Synthesis of (±)-Ginkgolide C and Formal Syntheses of (±)-Ginkgolides A and B
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Full item details
- dc.contributor.author
- Barriault, Louis
- Hébert, Martin
- Bellavance, Gabriel
- dc.date.accepted
- 2025-06-18
- dc.date.accessioned
- 2026-02-04T20:12:05Z
- dc.date.available
- 2026-02-04T20:12:05Z
- dc.date.issued
- 2025-06-25
- dc.date.submitted
- 2025-04-26
- dc.description.abstract - en
- Ginkgolides are highly oxygenated diterpenes isolated from Ginkgo biloba that exhibit potent anti-inflammatory and neuroprotective properties. Their compact hexacyclic architecture—featuring multiple contiguous stereocenters, a spirocyclic core, and a rare tert-butyl group—presents a formidable challenge in synthetic organic chemistry. Herein, we report the first total synthesis of ginkgolide C (3), the most structurally complex member of this family, completed in 26 steps from commercially available materials. The synthesis is guided by a functional group–driven strategy that enables the convergent construction of the polycyclic core through key diastereoselective carbon–carbon bond formations, selective oxidations, and late-stage epoxide-opening lactonizations. In parallel, the formal syntheses of ginkgolides A (1) and B (2) were accomplished via interception of a late-stage intermediate in 17 steps, the shortest route to these targets reported to date. This work provides a unified synthetic platform for accessing the ginkgolide family and offers new opportunities for the synthesis and biological evaluation of related analogues.
- dc.description.fosrcfull - en
- This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © 2025 American Chemical Society after peer review. To access the final edited and published work see <a href="https://doi.org/10.1021/acs.joc.5c01012">https://doi.org/10.1021/acs.joc.5c01012</a>.
- dc.description.fosrcfull-fosrctranslation - fr
- Ce document est la version non éditée d'un travail soumis par l'auteur qui a été accepté pour publication dans The Journal of Organic Chemistry, droit d'auteur © 2025 American Chemical Society après évaluation par les pairs. Pour accéder au travail final édité et publié, voir <a href="https://doi.org/10.1021/acs.joc.5c01012">https://doi.org/10.1021/acs.joc.5c01012</a>.
- dc.identifier.doi
- https://doi.org/10.26434/chemrxiv-2025-ppm63
- dc.identifier.issn
- 0022-3263
- 1520-6904
- dc.identifier.uri
- https://open-science.canada.ca/handle/123456789/4188
- dc.language.iso
- en
- dc.publisher - en
- American Chemical Society
- dc.publisher - fr
- American Chemical Society
- dc.relation.isreplacedby
- https://doi.org/10.1021/acs.joc.5c01012
- dc.rights - en
- Other
- dc.rights - fr
- Autre
- dc.rights.openaccesslevel - en
- Green
- dc.rights.openaccesslevel - fr
- Vert
- dc.rights.uri - en
- #description-element
- dc.rights.uri - fr
- #description-element
- dc.subject - en
- Chemistry
- Health
- Trees
- dc.subject - fr
- Chimie
- Santé
- Arbre
- dc.subject.en - en
- Chemistry
- Health
- Trees
- dc.subject.fr - fr
- Chimie
- Santé
- Arbre
- dc.title - en
- Advanced Synthetic Strategies toward Ginkgolide Diterpenoids: Total Synthesis of (±)-Ginkgolide C and Formal Syntheses of (±)-Ginkgolides A and B
- dc.type - en
- Submitted manuscript
- dc.type - fr
- Manuscrit soumis
- local.article.journalissue
- 26
- local.article.journaltitle - en
- The Journal of Organic Chemistry
- local.article.journalvolume
- 90
- local.pagination
- 27 pages
- local.peerreview - en
- No
- local.peerreview - fr
- Non
- local.requestdoi - en
- No
- local.requestdoi - fr
- No
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