Short Enantioselective Total Synthesis of Tatanan A and 3-epi-Tatanan A Using Assembly-Line Synthesis

Noble, A, Roesner, S ORCID: 0000-0003-2143-4708 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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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
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 and Biomolecular Sciences
Publisher:	Wiley
Date of acceptance:	4 November 2016
Date of first compliant Open Access:	23 April 2024
Date Deposited:	23 Apr 2024 13:04
Last Modified:	04 Jul 2025 12:30
DOI or ID number:	10.1002/anie.201609598
URI:	https://researchonline.ljmu.ac.uk/id/eprint/23119

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