ArticleJournal of the American Chemical Society2021
Stereocontrolled Radical Bicyclizations of Oxygenated Precursors Enable Short Syntheses of Oxidized Abietane Diterpenoids.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 67 citations in OpenAlex.
- Unexpected Regiochemical Control in the Nugent-RajanBabu Reductive Epoxide Cyclization.Synthesis · 2025Article
- Natural Product Synthesis Enabled by Radical-Polar Crossover Reactions.The Journal of organic chemistry · 2025Review
- Article
- Directed Hydrogen Atom Transfer for Selective Reactions of Polyenols.Journal of the American Chemical Society · 2024Article
- Unified short syntheses of oxygenated tricyclic aromatic diterpenes by radical cyclization with a photoredox catalyst.Communications chemistry · 2023Article
- Synthesis of a Complex Brasilicardin Analogue Utilizing a Cobalt-Catalyzed MHAT-Induced Radical Bicyclization Reaction.Organic letters · 2023Article
- Hydrogen-Atom-Transfer-Initiated Radical/Polar Crossover Annulation Cascade for Expedient Access to Complex Tetralins.Angewandte Chemie (International ed. in English) · 2023Article
- Toward the Asymmetric de Novo Synthesis of Lanostanes: Construction of 7,11-Dideoxy-ΔThe Journal of organic chemistry · 2022Article
- Programmed Polyene Cyclization Enabled by Chromophore Disruption.Journal of the American Chemical Society · 2022Article
- Total Synthesis of Natural Terpenoids Enabled by Cobalt Catalysis.Frontiers in chemistry · 2022Review
- Stereocontrolled Synthesis and Structural Revision of Plebeianiol A.Organic letters · 2021Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
The power of cation-initiated cyclizations of polyenes for the synthesis of polycyclic terpenoids cannot be overstated. However, a major limitation is the intolerance of many relevant reaction conditions toward the inclusion in the substrate of polar functionality, particularly in unprotected form. Radical polycyclizations are important alternatives to bioinspired cationic variants, in part owing to the range of possible initiation strategies, and in part for the functional group tolerance of radical reactions. In this article, we demonstrate that Co-catalyzed MHAT-initiated radical bicyclizations are not only tolerant of oxidation at virtually every position in the substrate, oftentimes in unprotected form, but these functional groups can also contribute to high levels of stereochemical control in these complexity-generating transformations. Specifically, we show the effects of protected or unprotected hydroxy groups at six different positions and their impact on stereoselectivity. Further, we show how multiply oxidized substrates perform in these reactions, and finally, we document the utility of these reactions in the synthesis of three aromatic abietane diterpenoids.
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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.