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The Total Synthesis and Structural Assignment of Hexaketide Xylarinol B and its C1′‐Epimer

The Total Synthesis and Structural Assignment of Hexaketide Xylarinol B and its C1′‐Epimer The total synthesis of two isomeric hexaketides isolated along with sordarial, which have the proposed relative arabino and ribo configurations, has been executed. A Rh‐catalyzed [2+2+2]‐alkyne cyclotrimerization has been employed as the key reaction to construct the central dihydroisobenzofuran core. The absolute configuration of the xylarinol B hexaketide has been established as l‐arabino. This is the first natural product of this family for which the absolute configuration has been determined, and this can be extended to provide structural details of several of related hexaketides. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Asian Journal of Organic Chemistry Wiley

The Total Synthesis and Structural Assignment of Hexaketide Xylarinol B and its C1′‐Epimer

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References (69)

Publisher
Wiley
Copyright
© 2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
ISSN
2193-5807
eISSN
2193-5815
DOI
10.1002/ajoc.201500511
Publisher site
See Article on Publisher Site

Abstract

The total synthesis of two isomeric hexaketides isolated along with sordarial, which have the proposed relative arabino and ribo configurations, has been executed. A Rh‐catalyzed [2+2+2]‐alkyne cyclotrimerization has been employed as the key reaction to construct the central dihydroisobenzofuran core. The absolute configuration of the xylarinol B hexaketide has been established as l‐arabino. This is the first natural product of this family for which the absolute configuration has been determined, and this can be extended to provide structural details of several of related hexaketides.

Journal

Asian Journal of Organic ChemistryWiley

Published: Mar 1, 2016

Keywords: ; ; ; ;

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