ArticleJournal of the American Chemical Society2011
Divergent synthesis and chemical reactivity of bicyclic lactone fragments of complex rearranged spongian diterpenes.
Article in Journal of the American Chemical Society, 2011. 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, 29 citations in OpenAlex.
- Synthesis ofThe Journal of organic chemistry · 2023Article
- Catalytic Hydroxycyclopropanol Ring-Opening Carbonylative Lactonization to Fused Bicyclic Lactones.Journal of the American Chemical Society · 2020Article
- Enantioselective Total Synthesis of Macfarlandin C, a Spongian Diterpenoid Harboring a Concave-Substituted cis-Dioxabicyclo[3.3.0]octanone Fragment.Angewandte Chemie (International ed. in English) · 2020Article
- Investigation of the electrophilic reactivity of the biologically active marine sesquiterpenoid onchidal and model compounds.Beilstein journal of organic chemistry · 2018Article
- Covalent modification of biological targets with natural products through Paal-Knorr pyrrole formation.Natural product reports · 2017Review
- Synthetic and Biological Studies of Sesquiterpene Polygodial: Activity of 9-Epipolygodial against Drug-Resistant Cancer Cells.ChemMedChem · 2015Article
- Wittig derivatization of sesquiterpenoid polygodial leads to cytostatic agents with activity against drug resistant cancer cells and capable of pyrrolylation of primary amines.European journal of medicinal chemistry · 2015Article
- Fungal metabolite ophiobolin A as a promising anti-glioma agent: In vivo evaluation, structure-activity relationship and unique pyrrolylation of primary amines.Bioorganic & medicinal chemistry letters · 2015Article
- Bioactive micronutrients in coffee: recent analytical approaches for characterization and quantification.ISRN nutrition · 2014Review
- A concise synthesis of (-)-aplyviolene facilitated by a strategic tertiary radical conjugate addition.Angewandte Chemie (International ed. in English) · 2012Article
- Enantioselective total synthesis of aplyviolene.Journal of the American Chemical Society · 2011Article
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
Abstract
The synthesis and direct comparison of the chemical reactivity of the two highly oxidized bicyclic lactone fragments found in rearranged spongian diterpenes (8-substituted 6-acetoxy-2,7-dioxabicyclo[3.2.1]octan-3-one and 6-substituted 7-acetoxy-2,8-dioxabicyclo[3.3.0]octan-3-one) are reported. Details of the first synthesis of the 6-acetoxy-2,7-dioxabicyclo[3.2.1]octan-3-one ring system, including an examination of several possibilities for the key bridging cyclization reaction, are described. In addition, the first synthesis of 7-acetoxy-2,8-dioxabicyclo[3.3.0]octanones containing quaternary carbon substituents at C6 is disclosed. Aspects of the chemical reactivity and Golgi-modifying properties of these bicyclic lactone analogs of rearranged spongian diterpenes are also reported. Under both acidic and basic conditions, 8-substituted 2,7-dioxabicyclo[3.2.1]octanones are converted to 6-substituted-2,8-dioxabicyclo[3.3.0]octanones. Moreover, these dioxabicyclic lactones react with primary amines and lysine side chains of lysozyme to form substituted pyrroles, a conjugation that could be responsible for the unique biological properties of these compounds. These studies demonstrate that acetoxylation adjacent to the lactone carbonyl group, in either the bridged or fused series, is required to produce fragmented Golgi membranes in the pericentriolar region that is characteristic of macfarlandin E.
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