An Olefin Cross-Metathesis Approach to Depudecin and Stereoisomeric Analogues

被引：7

作者：

Cheng-Sanchez, Ivan ^{[1
]}

Garcia-Ruiz, Cristina ^{[1
,2
]}

Guerrero-Vasquez, Guillermo A. ^{[1
]}

Sarabia, Francisco ^{[1
]}

机构：

[1] Univ Malaga, Dept Organ Chem, Fac Sci, Campus Teatinos S-N, E-29071 Malaga, Spain

[2] Univ Bristol, Sch Chem, Cantocks Close, Bristol BS8 1TS, Avon, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 09期

关键词：

HISTONE DEACETYLASE INHIBITORS; STEREOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC TOTAL-SYNTHESIS; CENTRAL-NERVOUS-SYSTEM; ALLYLIC ALCOHOLS; GLYCIDIC AMIDES; ALTERNARIA-BRASSICICOLA; ANTITUMOR AGENTS; GENE-EXPRESSION; HDAC INHIBITORS;

D O I：

10.1021/acs.joc.7b00424

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new total synthesis of the natural product (-)-depudecin, a unique and unexplored histone deacetylase (HDAC) inhibitor, is reported. A key feature of the synthesis is the utilization of an olefin cross-metathesis strategy, which provides for an efficient and improved access to natural depudecin, compared with our previous linear synthesis. Featured by its brevity and convergency, our developed synthetic strategy was applied to the preparation of the 10-epi derivative and the enantiomer of depudecin, which represent interesting stereoisomeric analogues for structure activity relationship studies.

引用

页码：4744 / 4757

页数：14

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