Concise, enantioselective, and versatile synthesis of (−)-Englerin A Based on a platinum-catalyzed [4C+3C] cycloaddition of allenedienes
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Title: | Concise, enantioselective, and versatile synthesis of (−)-Englerin A Based on a platinum-catalyzed [4C+3C] cycloaddition of allenedienes |
Author: | Nelson, Ronald Gulías Costa, Moisés Mascareñas Cid, José Luis López García, Fernando |
Affiliation: | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares Universidade de Santiago de Compostela. Departamento de Química Orgánica |
Subject: | Englerin-A | Achiral precursors | Cycloaddition | Allenes | Asymmetric catalysis | Guaiane natural products | Total synthesis | |
Date of Issue: | 2016-10-13 |
Publisher: | WILEY-VCH Verlag GmbH |
Citation: | R. Nelson, M. Gulías, J. L. Mascareñas, F. López, Angew. Chem. Int. Ed. 2016, 55, 14359 |
Abstract: | A practical synthesis of (−)-englerin A was accomplished in 17 steps and 11 % global yield from commercially available achiral precursors. The key step consists of a platinum-catalyzed [4C+3C] allenediene cycloaddition that directly delivers the trans-fused guaiane skeleton with complete diastereoselectivity. The high enantioselectivity (99 % ee) stems from an asymmetric ruthenium-catalyzed transfer hydrogenation of a readily assembled diene–ynone. The synthesis also features a highly stereoselective oxygenation, and a late-stage cuprate alkylation that enables the preparation of previously inaccessible structural analogues |
Description: | NOTICE: This is the peer reviewed version of the following article: Ronald Nelson, Moisés Gulías, José L. Mascareñas*, Fernando López* (2016), A Concise, Enantioselective and Versatile Synthesis of (-)-Englerin A based on a Pt-catalyzed [4C+3C] Cycloaddition of Allenedienes, Angew. Chem. Int. Ed., 55, 1-6 [doi:10.1002/anie.201607348]. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for self-archiving |
Publisher version: | http://dx.doi.org/10.1002/anie.201607348 |
URI: | http://hdl.handle.net/10347/15018 |
DOI: | 10.1002/anie.201607348 |
E-ISSN: | 1521-3773 |
Rights: | © WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
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