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 inAsian journal of organic chemistry Vol. 5; no. 3; pp. 417 - 422
Main Authors Mullapudi, Venkannababu, Ramana, Chepuri V.
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.03.2016
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
xylarinolB
sordarial
METABOLITES
COMPLEXES
SORDARIOL
FORMAL TOTAL-SYNTHESIS
hexaketides
ALKYNE
CATALYZED 2+2+2 CYCLOADDITION
Wilkinson's catalyst
CYCLIZATIONS
[2+2+2]-cyclotrimerization
CONSTRUCTION
DERIVATIVES
DIYNES
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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