The Total Synthesis and Structural Assignment of Hexaketide XylarinolB and its C1-Epimer

被引：10

作者：

Mullapudi, Venkannababu ^{[1
]}

Ramana, Chepuri V. ^{[1
]}

机构：

[1] CSIR, Natl Chem Lab, Div Organ Chem, Pune 411008, Maharashtra, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 03期

关键词：

2+2+2]-cyclotrimerization; hexaketides; sordarial; Wilkinson's catalyst; xylarinolB; CATALYZED 2+2+2 CYCLOADDITION; FORMAL TOTAL-SYNTHESIS; CONSTRUCTION; CYCLIZATIONS; METABOLITES; DERIVATIVES; COMPLEXES; SORDARIOL; DIYNES; ALKYNE;

D O I：

10.1002/ajoc.201500511

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：417 / 422

页数：6

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