ArticleJournal of the American Chemical Society2022
Asymmetric Total Synthesis of Havellockate.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 29 citations in OpenAlex.
- Asymmetric Total Synthesis of (+)-Ineleganolide.Angewandte Chemie (International ed. in English) · 2026Article
- The Diels-Alder Reaction as a Key Step in Natural Product Synthesis.Progress in the chemistry of organic natural products · 2026Review
- Fast Esterification Method Mediated by Coupling Reagent NDTP.ACS omega · 2025Article
- Recent advancements in the chemistry of Diels-Alder reaction for total synthesis of natural products: a comprehensive review (2020-2023).RSC advances · 2025Review
- Biomimetic Synthesis of Azorellolide via Cyclopropylcarbinyl Cation Chemistry.Journal of the American Chemical Society · 2025Article
- Accessing the synthesis of natural products and their analogues enabled by the Barbier reaction: a review.RSC advances · 2024Review
- Systematic Route to Construct the 5-5-6 Tricyclic Core of Furanobutenolide-Derived Cembranoids and Norcembranoids.Organic letters · 2024Article
- Convenient Access to a Strained Bicyclic Enone: A Concise and Improved Formal Synthesis of Ineleganolide.Tetrahedron letters · 2024Article
- Steglich esterification: A versatile synthetic approach toward the synthesis of natural products, their analogues/derivatives.Heliyon · 2024Article
- General acid-mediated aminolactone formation using unactivated alkenes.Chemical science · 2023Article
- Total synthesis of (-)-scabrolide A and (-)-yonarolide.Chemical science · 2023Article
- A Convergent Total Synthesis of (+)-Ineleganolide.Journal of the American Chemical Society · 2023Article
Corrections and comments
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Authors and funding
7 authors at 1 institution in 1 country.
Funding
Abstract
The first total synthesis of the furanobutenolide-derived cembranoid diterpenoid havellockate is disclosed. Our convergent strategy employs a Julia-Kocienski olefination to join two enantioenriched fragments to produce a diene that is subsequently used in a propiolic acid esterification/Diels-Alder cascade. This sequence generates the fused carbocyclic core of the natural product in short order. A challenging Zn-mediated Barbier allylation then forges the final C-C bond and also establishes two vicinal stereogenic centers. Finally, a Cu-catalyzed aerobic oxidation facilitates the formation of the β-hydroxybutanolide to complete the total synthesis.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.