First total synthesis of natural andytriol and a biomimetic approach to varioxiranes

被引：4

作者：

Markovic, Martin ^{[1
]}

Lopatka, Pavol ^{[1
]}

Koos, Peter ^{[2
]}

Gracza, Tibor ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, SK-81237 Bratislava, Slovakia

[2] Georganics Ltd, SK-81103 Bratislava, Slovakia

来源：

TETRAHEDRON | 2015年 / 71卷 / 44期

关键词：

Natural products; Andytriol; Varioxirane; Emericella variecolor; Biomimetic synthesis; UNSATURATED POLYOLS; PALLADIUM(II)-CATALYZED OXYCARBONYLATION; ASYMMETRIC EPOXIDATION; EMERICELLA-VARIECOLOR; METABOLITES; (+)-VARITRIOL; CONDENSATION; DERIVATIVES; VARITRIOL; SULFONES;

D O I：

10.1016/j.tet.2015.09.002

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first diastereoselective synthesis of natural fungal metabolite (+)-andytriol 1, the proposed biosynthetic precursor of varioxirane, was accomplished in nine linear steps from 2,3-O-isopropylidene-D-ribose. A biomimetic Katsuki-Sharpless epoxidation was then applied to construct the oxirane ring of the varioxiranes. The absolute configuration of the target molecule (+)-1 was for the first time confirmed by the single X-ray analysis. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：8407 / 8415

页数：9

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