Total Synthesis of Englerin A

Total synthesis of englerin A, a recently reported sesquiterpenoid exhibiting potent and selective growth inhibition against renal cancer cell lines, has been accomplished. The successful strategy featured a [5 + 2] cycloaddition reaction to cast the seven-membered oxabicyclic key intermediate in bo...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 132; no. 23; pp. 8219 - 8222
Main Authors Nicolaou, K. C, Kang, Qiang, Ng, Sin Yee, Chen, David Y.-K
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.06.2010
Amer Chemical Soc
Subjects
Acetates - chemistry
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Cell Line, Tumor
Chemistry
Chemistry, Multidisciplinary
Esters - chemistry
Humans
Inhibitory Concentration 50
Kidney Neoplasms - pathology
Physical Sciences
Science & Technology
Sesquiterpenes, Guaiane - chemical synthesis
Sesquiterpenes, Guaiane - chemistry
Sesquiterpenes, Guaiane - pharmacology
Stereoisomerism
KETONES
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Summary:Total synthesis of englerin A, a recently reported sesquiterpenoid exhibiting potent and selective growth inhibition against renal cancer cell lines, has been accomplished. The successful strategy featured a [5 + 2] cycloaddition reaction to cast the seven-membered oxabicyclic key intermediate in both racemic and optically active forms. Synthetic (±)-englerin A, (±)-englerin B, (±)-englerin B acetate, a hydroxy acetate, a tert-butyldimethylsilyl ether, and hydrogenated (±)-englerin A (31) were tested for their cytotoxicity against a selected panel of cancer cell lines, and the results are path-pointing to more focused structure−activity relationship studies.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
DOI:10.1021/ja102927n