ArticleJournal of the American Chemical Society2013
Enantio- and diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Article
- Modular Chemoenzymatic Synthesis of GE81112 B1 and Related Analogues Enables Elucidation of Its Key Pharmacophores.Journal of the American Chemical Society · 2021Article
- Formation of Nucleophilic Allylboranes from Molecular Hydrogen and Allenes Catalyzed by a Pyridonate Borane that Displays Frustrated Lewis Pair Reactivity.Angewandte Chemie (International ed. in English) · 2020Article
- Uridine natural products: Challenging targets and inspiration for novel small molecule inhibitors.Bioorganic & medicinal chemistry · 2020Review
- Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin.Organic letters · 2014Article
- Enantioselective synthesis of (Z)- and (E)-2-methyl-1,5-anti-pentenediols via an allene hydroboration-double-allylboration reaction sequence.Journal of the American Chemical Society · 2013Article
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Authors and funding
2 authors.
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Abstract
A highly diastereoselective synthesis of N-acetyl dihydrotetrafibricin methyl ester (34) is described. The synthesis features three enantioselective double allylboration reactions and an intramolecular hydrosilylation/Fleming-Tamao oxidation sequence to establish seven of the hydroxy-bearing stereocenters of 34. Especially noteworthy is the fragment-assembly double allyboration reaction of 2 and 7 using reagent 3, which provides the advanced intermediate 6 with >20:1 diastereoselectivity.
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