Enantioselective total synthesis of altersolanol A and N

被引：1

作者：

Mechsner, Bastian ^{[1
]}

Boese, Dietrich ^{[1
]}

Hogenkamp, Fabian ^{[1
]}

Ledermann, Nadia ^{[1
]}

Hartmann, Rudolf ^{[2
]}

Bochinsky, Kevin ^{[2
]}

Frey, Wolfgang ^{[3
]}

Pietruszka, Joerg ^{[1
,4
]}

机构：

[1] Heinrich Heine Univ Dusseldorf, Forschungszentrum Julich, Inst Bioorgan Chem IBOC, Stetternicher Forst, Geb 15-8, D-52426 Julich, Germany

[2] Forschungszentrum Julich, Inst Complex Syst Strukturbiochem, Wilhelm Johnen Str, D-52428 Julich, Germany

[3] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany

[4] Forschungszentrum Julich, IBG 1 Biotechnol, D-52428 Julich, Germany

来源：

BIOORGANIC & MEDICINAL CHEMISTRY | 2019年 / 27卷 / 13期

关键词：

Natural product; Asymmetric synthesis; Enantioselectivity; Diels-Alder reaction; DIELS-ALDER REACTIONS; FUNGUS STEMPHYLIUM-GLOBULIFERUM; ALTERNARIA-PORRI; ORTHOESTERS; METABOLITES; DIENOPHILES; SCOPE;

D O I：

10.1016/j.bmc.2019.04.033

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The development of the first enantioselective total synthesis of altersolanol N is reported. The decisive step of the synthesis is the enantioselective formation of the tetrahydroanthraquinone nucleus by a [4+ 2]-cycloaddition in high yield and with excellent diastereo-and enantioselectivity (> 95: 5 dr and 95: 5 er). In addition, a demanding selective monoacetylation of the OH group at the C-2 position was achieved: an epoxide ring opening with the participation of a neighbouring acetyl group could be established. The route proved to be an efficient alternative to also access enantiomerically pure altersolanol A.

引用

页码：2991 / 2997

页数：7

共 55 条

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