1311401-97-4

Upstream product

• 1147862-00-7 1,5-bis((tert-butyldimethylsilyl)oxy)cyclohexa-1,4-diene 
• 1147862-12-1 (1R,3R,4R,6R)-4,6-bis(tert-butyldimethylsilyloxy)cyclohexane-1,3-diol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1147862-11-0 (1R,3R,5R,7R)-1,3-(tert-butyldimethylsilyloxy)-4,8-dioxatricyclo[5.1.0.0]octane 

Downstream Products

• 1311401-99-6 C₁₈H₃₇IO₃Si₂ 
• 1311402-03-5 C₂₉H₅₁BrO₈Si₂ 

Relevant academic research and scientific papers

Enantioselective total synthesis of ( - )-kibdelone C

The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C - H arylation to complete the hexacyclic skeleton.

Synthesis and Biological Evaluation of Kibdelone C and Its Simplified Derivatives

Poylcyclic tetrahydroxanthones comprise a large class of cytototoxic natural products. No mechanism of action has been described for any member of the family. We report the synthesis of kibdelone C and several simplified analogs. Both enantiomers of kibdeleone C show low nanomolar cytotoxicity toward multiple human cancer cell lines. Moreover, several simplified derivatives with improved chemical stability display higher activity than the natural product itself. In vitro studies rule out interaction with DNA or inhibition of topoisomerase, both of which are common modes of action for polycyclic aromatic compounds. However, celluar studies reveal that kibdelone C and its simplified derivatives disrupt the actin cytoseketon without directly binding actin or affecting its polymerization in vitro.