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Short enantioselective total synthesis of tatanan A and 3-epi-tatanan A using assembly-line synthesis
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Noble, Adam, Roesner, Stefan and Aggarwal, Varinder K. (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. doi:10.1002/anie.201609598 ISSN 1433-7851.
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Official URL: http://dx.doi.org/10.1002/anie.201609598
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: | Journal Article | |||||||||
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Subjects: | Q Science > QD Chemistry | |||||||||
Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | |||||||||
Library of Congress Subject Headings (LCSH): | Chemistry., Organic compounds -- Synthesis. | |||||||||
Journal or Publication Title: | Angewandte Chemie International Edition | |||||||||
Publisher: | Wiley - V C H Verlag GmbH & Co. KGaA | |||||||||
ISSN: | 1433-7851 | |||||||||
Official Date: | 12 December 2016 | |||||||||
Dates: |
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Volume: | 55 | |||||||||
Number: | 51 | |||||||||
Page Range: | pp. 15920-15924 | |||||||||
DOI: | 10.1002/anie.201609598 | |||||||||
Status: | Peer Reviewed | |||||||||
Publication Status: | Published | |||||||||
Access rights to Published version: | Open Access (Creative Commons) | |||||||||
Date of first compliant deposit: | 12 December 2017 | |||||||||
Date of first compliant Open Access: | 12 December 2017 | |||||||||
RIOXX Funder/Project Grant: |
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