Total synthesis of englerin A.

Abstract

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.

• Authors: K C Nicolaou, Qiang Kang, Sin Yee Ng, David Y-K Chen
• Journal: Journal of the American Chemical Society (J Am Chem Soc) Vol. 132 Issue 23 Pg. 8219-22 (Jun 16 2010) ISSN: 1520-5126 [Electronic] United States
• PMID: 20496885 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Acetates
• Antineoplastic Agents
• Esters
• Sesquiterpenes, Guaiane
• englerin A
• englerin B

Topics

• Acetates (chemistry)
• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Cell Line, Tumor
• Esters (chemistry)
• Humans
• Inhibitory Concentration 50
• Kidney Neoplasms (pathology)
• Sesquiterpenes, Guaiane (chemical synthesis, chemistry, pharmacology)
• Stereoisomerism