First Total Synthesis of Varioxiranol A

被引：4

作者：

Lasikova, Angelika ^{[1
]}

Dohanosova, Jana ^{[2
]}

Stiblarikova, Maria ^{[1
]}

Parak, Martin ^{[1
]}

Moncol, Jan ^{[3
]}

Gracza, Tibor ^{[1
]}

机构：

[1] Slovak Univ Technol Bratislava, Dept Organ Chem, Radlinskeho 9, Bratislava 81237, Slovakia

[2] Slovak Univ Technol Bratislava, Cent Labs, Radlinskeho 9, Bratislava 81237, Slovakia

[3] Slovak Univ Technol Bratislava, Dept Inorgan Chem, Radlinskeho 9, Bratislava 81237, Slovakia

来源：

MOLECULES | 2019年 / 24卷 / 05期

关键词：

synthesis of natural products; varioxiranol A; 4-epi-varioxiranol A; absolute structure; Emericella variecolor; METABOLITES; FUNGUS;

D O I：

10.3390/molecules24050862

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 paper describes the first total synthesis of natural varioxiranol A by chiral pool approach and confirmation of its absolute configuration by single-crystal X-ray analysis. The target varioxiranol A and its 4-epimer were obtained after 10 steps from single and available chiral source 1,2-O-isopropylidene-D-glyceraldehyde in an overall yield of 10% and 6%, respectively. A synthetic strategy based on the Julia-Kocienski coupling reaction between aromatic sulfone and corresponding aldose derivative makes it possible to prepare other interesting polyketide derivatives (varioxiranols B-G, varioxirane, varioxiranediols).

引用

页数：11

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