ArticleOrganic letters2015
A concise synthetic route to the stereotetrad core of the briarane diterpenoids.
Article in Organic letters, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Orally Bioavailable and Site-Selective Covalent STING Inhibitor Derived from a Macrocyclic Marine Diterpenoid.Journal of medicinal chemistry · 2025Article
- Marine diterpenoid targets STING palmitoylation in mammalian cells.Communications chemistry · 2023Article
- Synthesis and Antimicrobial Activity of the PathogenicInternational journal of molecular sciences · 2023Article
- Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.Chemical reviews · 2020Review
- Article
- Synthetic explorations of the briarane jungle: progress in developing a synthetic route to a common family of diterpenoid natural products.Royal Society open science · 2018Review
- Torsional steering as friend and foe: development of a synthetic route to the briarane diterpenoid stereotetrad.Organic & biomolecular chemistry · 2017Article
- Briarane Diterpenoids Isolated from Octocorals between 2014 and 2016.Marine drugs · 2017Review
Corrections and comments
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Authors and funding
2 authors.
Funding
Abstract
A concise synthesis (under 10 steps) of the stereotetrad core of the briarane diterpenoids is reported. This approach harnesses the unique reactivity of salicylate ester derived 2,5-cyclohexadienones to quickly build complexity. In particular, a highly diastereoselective acetylide conjugate addition/β-ketoester alkylation sequence was used to set the relative configuration of the C1 (quaternary) and C10 (tertiary) vicinal stereocenters. The sterochemical outcome of the β-ketoester alkylation appears to be governed by torsional steering in the transition state.
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