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 cor...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2016-03, Vol.5 (3), p.417-422
Main Authors: Mullapudi, Venkannababu, Ramana, Chepuri V.
Format: Article
Language:English
Subjects:
[2+2+2]-cyclotrimerization
hexaketides
sordarial
Wilkinson's catalyst
xylarinol B
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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 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. Hex appeal: By following a chiral‐pool approach and employing a Rh‐catalyzed [2+2+2]‐alkyne cyclotrimerization to construct the key isobenzofuran core, the total synthesis of xylarinol B hexaketide and its C(1)‐epimer have been executed to fix their relative and absolute configurations, as a first step towards providing the structural details of several related hexaketides.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201500511