Stereoselective Chemoenzymatic Cascade Synthesis of the bis-THF Core of Acetogenins

被引：4

作者：

van Lint, Matthijs J. ^{[1
]}

Hall, Melanie ^{[2
]}

Faber, Kurt ^{[2
]}

van Spanning, Rob J. M. ^{[1
]}

Ruijter, Eelco ^{[1
]}

Orru, Romano V. A. ^{[1
]}

机构：

[1] Vrije Univ Amsterdam, Amsterdam Inst Mol Med & Syst, De Boelelaan 1108, NL-1081 HZ Amsterdam, Netherlands

[2] Karl Franzens Univ Graz, Dept Chem Organ & Bioorgan Chem, Heinrichstr 28, A-8010 Graz, Austria

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 2019卷 / 05期

关键词：

Acetogenins; Chemoenzymatic synthesis; Epoxide hydrolases; Natural products; Stereoselective synthesis; COUNTERANION-DIRECTED CATALYSIS; ANNONACEOUS ACETOGENINS; ADJACENT BISTETRAHYDROFURAN; ASIMICIN; GIGANTETROCIN; EPOXIDATION; ANALOGS;

D O I：

10.1002/ejoc.201801562

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

bis-Tetrahydrofuran acetogenins are a class of natural products displaying highly potent and selective anti-tumor activity. Herein we report a new route to precursors of these natural products, utilizing the pseudo C-2-symmetry in the central bis-tetrahydrofuran fragment. Key steps of our stereoselective chemoenzymatic strategy include the epoxide hydrolase-mediated desymmetrization of meso-epoxides and a cascade cyclization in either "inside-out" or "outside-in" direction, providing stereoselective access to the cores of both bullatacin- and rolliniastatin 1-type acetogenins with 6 stereocenters each from a common mono-epoxide precursor.

引用

页码：1092 / 1101

页数：10

共 53 条

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