Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A

Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐cl...

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Autores principales: Millán, Alba, Smith, James R., Chen, Jack L.‐Y., Aggarwal, Varinder K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4755224/
https://www.ncbi.nlm.nih.gov/pubmed/26766494
http://dx.doi.org/10.1002/anie.201511140
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author Millán, Alba
Smith, James R.
Chen, Jack L.‐Y.
Aggarwal, Varinder K.
author_facet Millán, Alba
Smith, James R.
Chen, Jack L.‐Y.
Aggarwal, Varinder K.
author_sort Millán, Alba
collection PubMed
description Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation‐borylation reaction to attach the cyclopropyl‐containing side chain.
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spelling pubmed-47552242016-06-22 Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A Millán, Alba Smith, James R. Chen, Jack L.‐Y. Aggarwal, Varinder K. Angew Chem Int Ed Engl Communications Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three‐component allylboration‐Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % overall yield) synthesis of the macrolide (−)‐clavosolide A. The synthesis also features an early stage glycosidation reaction to introduce the xylose moiety and a lithiation‐borylation reaction to attach the cyclopropyl‐containing side chain. John Wiley and Sons Inc. 2016-01-14 2016-02-12 /pmc/articles/PMC4755224/ /pubmed/26766494 http://dx.doi.org/10.1002/anie.201511140 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Millán, Alba
Smith, James R.
Chen, Jack L.‐Y.
Aggarwal, Varinder K.
Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
title Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
title_full Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
title_fullStr Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
title_full_unstemmed Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
title_short Tandem Allylboration–Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (−)‐Clavosolide A
title_sort tandem allylboration–prins reaction for the rapid construction of substituted tetrahydropyrans: application to the total synthesis of (−)‐clavosolide a
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4755224/
https://www.ncbi.nlm.nih.gov/pubmed/26766494
http://dx.doi.org/10.1002/anie.201511140
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