ArticleAngewandte Chemie (International ed. in English)2020
Asymmetric Total Syntheses of Di- and Sesquiterpenoids by Catalytic C-C Activation of Cyclopentanones.
Article in Angewandte Chemie (International ed. in English), 2020. 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, 26 citations in OpenAlex.
- Skeletal Modification via Activation of Relatively Unstrained C-C Bonds.Accounts of chemical research · 2025Article
- Deconstructive and Divergent Synthesis of Bioactive Natural Products.Molecules (Basel, Switzerland) · 2023Review
- The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.Chemical communications (Cambridge, England) · 2022Review
- Autoxidation of a C2-Olefinated Dihydroartemisinic Acid Analogue to Form an Aromatic Ring: Application to Serrulatene Biosynthesis.Journal of natural products · 2022Review
- Studies on the Lithiation, Borylation, and 1,2-Metalate Rearrangement of O-Cycloalkyl 2,4,6-Triisopropylbenzoates.Angewandte Chemie (International ed. in English) · 2021Article
- Temporary or removable directing groups enable activation of unstrained C-C bonds.Nature reviews. Chemistry · 2020Article
- Regiodivergent C-H and Decarboxylative C-C Alkylation by Ruthenium Catalysis: ortho versus meta Position-Selectivity.Angewandte Chemie (International ed. in English) · 2020Article
- Asymmetric Synthesis of 1-Tetralones Bearing A Remote Quaternary Stereocenter through Rh-Catalyzed C-C Activation of Cyclopentanones.Bulletin of the Chemical Society of Japan · 2020Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
To show the synthetic utility of the catalytic C-C activation of less strained substrates, described here are the collective and concise syntheses of the natural products (-)-microthecaline A, (-)-leubehanol, (+)-pseudopteroxazole, (+)-seco-pseudopteroxazole, pseudopterosin A-F and G-J aglycones, and (+)-heritonin. The key step in these syntheses involve a Rh-catalyzed C-C/C-H activation cascade of 3-arylcyclopentanones, which provides a rapid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products. Other important features include 1) the direct C-H amination of the tetralone substrate in the synthesis of (-)-microthecaline A, 2) the use of phosphoric acid to enhance efficiency and regioselectivity for problematic cyclopentanone substrates in the C-C activation reactions, and 3) the direct conversion of serrulatane into amphilectane diterpenes by an allylic cyclodehydrogenation coupling.
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