Total Synthesis and Configurational Assignment of the Marine Natural Product Haliclamide

被引：8

作者：

Pfeiffer, Bernhard ^{[1
]}

Speck-Gisler, Sandra ^{[1
]}

Barandun, Luzi ^{[1
]}

Senft, Ursula ^{[1
]}

de Groot, Claire ^{[1
]}

Lehmann, Irene ^{[2
]}

Ganci, Walter ^{[2
]}

Gertsch, Juerg ^{[1
]}

Altmann, Karl-Heinz ^{[1
]}

机构：

[1] ETH, Dept Chem & Appl Biosci, Inst Pharmaceut Sci, CH-8093 Zurich, Switzerland

[2] Univ Zurich, Inst Organ Chem, Lab Proc Res, CH-8057 Zurich, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期

关键词：

D-AMINO ACIDS; PEPTIDE; SPONGE; CYCLODEPSIPEPTIDE; JASPLAKINOLIDE; CHONDRAMIDES; MYXOBACTERIA; ANTIFUNGAL; MACROLIDE; REAGENT;

D O I：

10.1021/jo3027643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The marine natural product haliclamide has been synthesized based on macrocyclization by ring-closing olefin metathesis. Using either enantiomer of two of the four building blocks that were employed to assemble the diene precursor for the metathesis reaction, three non-natural isomers of haliclamide were also prepared. On the basis of the comparison of the H-1 and C-13 NMR spectra of the individual stereoisomers with literature data for the natural product, the configuration of the previously unassigned stereocenters at C9 and C20 of haliclamide could be determined to be S for both carbons. The absolute configuration of haliclamide thus is 2S, 9S, 14R, 20S. The antiproliferative activity of synthetic haliclamide against several human cancer cell lines was found to be in the high mu M range. The compound showed no antifungal or antibiotic activity.

引用

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页码：2553 / 2563

页数：11

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