Isolation and Asymmetric Total Synthesis of Fungal Secondary Metabolite Hygrophorone B12

被引：18

作者：

Bette, Eileen ^{[1
]}

Otto, Alexander ^{[1
]}

Draeger, Tobias ^{[1
]}

Merzweiler, Kurt ^{[2
]}

Arnold, Norbert ^{[1
]}

Wessjohann, Ludger ^{[1
,3
]}

Westermann, Bernhard ^{[1
,3
]}

机构：

[1] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Germany

[2] Univ Halle Wittenberg, Inst Inorgan Chem, D-06120 Halle, Germany

[3] Univ Halle Wittenberg, Inst Organ Chem, D-06120 Halle, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 11期

关键词：

Total synthesis; Asymmetric synthesis; Natural products; Fungal constituents; Configuration determination; Structure elucidation;

D O I：

10.1002/ejoc.201403455

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hygrophorone B-12, a new antifungal constituent from the fruiting bodies of Hygrophorus abieticola, has been isolated and subsquently synthesized in enantiomerically pure form. The total synthesis includes a Sharpless asymmetric dihydroxylation protocol as the stereodifferentiating step, followed by two diastereoselective aldol-type reactions. The approach allows the unambiguous control of all three stereogenic centres, and, furthermore, unequivocal determination of the relative and absolute configuration of antibiotic hygrophorones B for the first time.

引用

页码：2357 / 2365

页数：9

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