ArticleAngewandte Chemie (International ed. in English)2016
Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis.
Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- Stereoselective Synthesis and Functionalization of Acetylenic Boronic Esters.Organic letters · 2026Article
- Functionalisation of homopropargyl boronic estersRSC advances · 2026Article
- Iterative Catalyst-Controlled Diastereoselective Matteson Homologations Enable the Selective Synthesis of Benzestrol Isomers.Journal of the American Chemical Society · 2024Article
- Synthesis of alkenyl boronates through stereoselective vinylene homologation of organoboronates.Nature synthesis · 2024Article
- Marine Puupehenone and Puupehedione: Synthesis and Future Perspectives.Marine drugs · 2023Review
- A Straightforward Synthesis of Polyketides via Ester Dienolate Matteson Homologation.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Stereospecific 1,2-Migrations of Boronate Complexes Induced by Electrophiles.Angewandte Chemie (International ed. in English) · 2020Review
- Iterative Assembly of Macrocyclic Lactones using Successive Ring Expansion Reactions.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
- The Molecular Industrial Revolution: Automated Synthesis of Small Molecules.Angewandte Chemie (International ed. in English) · 2018Review
- Toward Generalization of Iterative Small Molecule Synthesis.Nature reviews. Chemistry · 2018Article
- Enantioselective γ-borylation of unsaturated amides and stereoretentive Suzuki-Miyaura cross-coupling.Chemical science · 2017Article
- Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis.Angewandte Chemie (International ed. in English) · 2016Article
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3 authors.
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Abstract
Short and highly stereoselective total syntheses of the sesquilignan natural product tatanan A and its C3 epimer are described. An assembly-line synthesis approach, using iterative lithiation-borylation reactions, was applied to install the three contiguous stereocenters with high enantio- and diastereoselectivity. One of the stereocenters was installed using a configurationally labile lithiated primary benzyl benzoate, resulting in high levels of substrate-controlled (undesired) diastereoselectivity. However, reversal of selectivity was achieved by using a novel diastereoselective Matteson homologation. Stereospecific alkynylation of a hindered secondary benzylic boronic ester enabled completion of the synthesis in a total of eight steps.
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