Design and Synthesis of C-1 Methoxycarbonyl Derivative of Narciclasine and Its Biological Activity

被引：1

作者：

Habaz, Lihi ^{[1
]}

Bedard, Korey ^{[1
]}

Smith, Mitchell ^{[2
]}

Du, Liqin ^{[2
]}

Kornienko, Alexander ^{[2
]}

Hudlicky, Tomas ^{[1
]}

机构：

[1] Brock Univ, Dept Chem, 1812 Sir Isaac Brock Way, St Catharines, ON L2S 3A1, Canada

[2] Texas State Univ, Dept Chem & Biochem, San Marcos, TX 78666 USA

来源：

MOLECULES | 2022年 / 27卷 / 12期

基金：

美国国家卫生研究院; 加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

narciclasine; chemoenzymatic; synthesis; enantioselective synthesis; natural products; toluene dioxygenase; PANCRATISTATIN; DIHYDROXYLATION; METABOLITES; REFINEMENT; PRODUCTS; HOMOLOGS; ANALOGS;

D O I：

10.3390/molecules27123809

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：

A 15-step chemoenzymatic total synthesis of C-1 methoxycarbonyl narciclasine (10) was accomplished. The synthesis began with the toluene dioxygenase-mediated dihydroxylation of ortho-dibromobenzene to provide the corresponding cis-dihydrodiol (12) as a single enantiomer. Further key steps included a nitroso Diels-Alder reaction and an intramolecular Heck cyclization. The C-1 homolog 10 was tested and evaluated for antiproliferative activity against natural narciclasine (1) as the positive control. Experimental and spectral data are reported for all novel compounds.

引用

页数：13

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