ArticleAngewandte Chemie (International ed. in English)2014
Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.
Article in Angewandte Chemie (International ed. in English), 2014. 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, 35 citations in OpenAlex.
- Anti-Inflammatory Halogenated Monoterpenes from the Red AlgaMarine drugs · 2023Article
- An α-chloroaldehyde-based formal synthesis of eribulin.Nature communications · 2023Article
- The Recurring Roles of Chlorine in Synthetic and Biological Studies of the Lissoclimides.Accounts of chemical research · 2021Review
- A Novel Polyhalogenated Monoterpene Induces Cell Cycle Arrest and Apoptosis in Breast Cancer Cells.Marine drugs · 2019Article
- Seaweed Secondary Metabolites In Vitro and In Vivo Anticancer Activity.Marine drugs · 2018Review
- Synthesis facilitates an understanding of the structural basis for translation inhibition by the lissoclimides.Nature chemistry · 2017Article
- Integrating Molecular Networking and Biological Assays To Target the Isolation of a Cytotoxic Cyclic Octapeptide, Samoamide A, from an American Samoan Marine Cyanobacterium.Journal of natural products · 2017Article
- Cytotoxic halogenated monoterpenes from Plocamium cartilagineum.Natural product research · 2017Article
- Stereoselective Halogenation in Natural Product Synthesis.Angewandte Chemie (International ed. in English) · 2016Review
- Selective bromochlorination of a homoallylic alcohol for the total synthesis of (-)-anverene.Beilstein journal of organic chemistry · 2016Article
- Highly Selective Synthesis of Halomon, Plocamenone, and Isoplocamenone.Journal of the American Chemical Society · 2015Article
Corrections and comments
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Authors and funding
6 authors at 4 institutions in 2 countries.
Funding
Abstract
The family of polyhalogenated monoterpenes from Plocamium counts over a hundred known members. Using glyceraldehyde acetonide as a chiral-pool precursor, an enantioselective and divergent strategy was developed that provides a blueprint for the synthesis of many of the small yet complex acyclic members of this family. The broad applicability of this approach is demonstrated with the short, eight-step synthesis of four natural products and three analogues. These syntheses are the first of any members of the acyclic polyhalogenated Plocamium monoterpenes and permitted the evaluation of their selectivity against a range of tumor cell lines.
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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.