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Noble, A, Roesner, S and Aggarwal, VK (2016) Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis. Angewandte Chemie - International Edition, 55 (51). pp. 15920-15924. ISSN 1433-7851
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Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis.pdf - Published Version Available under License Creative Commons Attribution. Download (4MB) | Preview |
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.
| Item Type: | Article |
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| Uncontrolled Keywords: | Matteson homologation; alkynylation; lithiation-borylation; tatanan A; total synthesis; 03 Chemical Sciences; Organic Chemistry |
| Subjects: | Q Science > QD Chemistry R Medicine > RS Pharmacy and materia medica |
| Divisions: | Pharmacy & Biomolecular Sciences |
| Publisher: | Wiley |
| SWORD Depositor: | A Symplectic |
| Date Deposited: | 23 Apr 2024 13:04 |
| Last Modified: | 24 Apr 2024 13:01 |
| DOI or ID number: | 10.1002/anie.201609598 |
| URI: | https://researchonline.ljmu.ac.uk/id/eprint/23119 |
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