The Total Synthesis and Structural Assignment of Hexaketide XylarinolB 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 cor...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2016-03, Vol.5 (3), p.417
Main Authors: Mullapudi, Venkannababu, Ramana, Chepuri V
Format: Article
Language:English
Subjects:
Organic chemistry
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Summary: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 xylarinolB 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.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201500511