Short Enantioselective Total Synthesis of Tatanan A and 3‐ epi ‐Tatanan A Using Assembly‐Line Synthesis
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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Short Enantioselective Total Synthesis of Tatanan A and 3‐ epi ‐Tatanan A Using Assembly‐Line Synthesis ; volume:128 ; number:51 ; year:2016 ; pages:16152-16156 ; extent:5
Angewandte Chemie ; 128, Heft 51 (2016), 16152-16156 (gesamt 5)
- Urheber
- DOI
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10.1002/ange.201609598
- URN
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urn:nbn:de:101:1-2022103007083995108844
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:29 MESZ
Datenpartner
Deutsche Nationalbibliothek. Bei Fragen zum Objekt wenden Sie sich bitte an den Datenpartner.
Beteiligte
- Noble, Adam
- Roesner, Stefan
- Aggarwal, Varinder K.
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