1240318-07-3

Upstream product

• 100-39-0 benzyl bromide 
• 1240318-05-1 (1R,5S)-5-isopropyl-1-methyl-2-methylene-8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 1240318-03-9 (1R,5S)-(R)-4,4-dimethyl-2-oxotetrahydrofuran-3-yl-3-[(tert-butyldimethylsilyl)oxy]-5-isopropyl-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene-2-carboxylate 
• 1240318-01-7 (3aR,4R,7S,8R)-8-((tert-butyldimethylsilyl)oxy)-7-isopropyl-1,4-dimethyl-3a,4,7,8-tetrahydro-4,7-epoxyazulen-2(3H)-one 
• 1240318-02-8 (1S,2S,4S,5R)-2-((tert-butyldimethylsilyl)oxy)-1-isopropyl-5-methyl-4-(2-oxobutyl)-8-oxabicyclo [3.2.1]oct-6-en-3-one 
• 1240318-10-8 C₁₈H₃₀O₃Si 
• 1240318-06-2 (1S,2S,5R)-2-hydroxy-1-isopropyl-5-methyl-4-methylene-8-oxabicyclo[3.2.1]oct-6-en-3-one 
• 80828-39-3 2-(1'-hydroxy-1'-methylethyl)-5-methylfuran 
• 10599-66-3 5-methyl-2-(1-methylethenyl)furan 
• 10504-05-9 5-methyl-2-(1-methylethyl)furan 
• 534-22-5 2-methylfuran 

Downstream Products

• 1240318-11-9 C₂₈H₄₄O₄Si 
• 1240318-12-0 C₃₄H₅₈O₄Si₂ 

Relevant academic research and scientific papers

Formal synthesis of (-)-englerin A and cytotoxicity studies of truncated englerins

An efficient formal synthesis of (-)-englerin A (1) is reported. The target molecule is a recently isolated guaiane sesquiterpene that possesses highly potent and selective activity against renal cancer cell-lines. Our enantioselective strategy involved the construction of the BC ring system of compound 1 through a RhII-catalyzed [4+3] cycloaddition reaction followed by subsequent attachment of the A ring through an intramolecular aldol condensation reaction. As such, this strategy allows the synthesis of truncated englerins. Evaluation of these analogues with the A498 renal cancer cell-line suggested that the A ring of englerin is crucial to its antiproliferative activity. Moreover, evaluation of these analogues led to the identification of potent growth-inhibitors of CEM cells with GI50 values in the range 1-3 μM.

Enantioselective formal synthesis of (-)-englerin A via a Rh-catalyzed [4 + 3] cycloaddition reaction

An enantioselective formal synthesis of (-)-englerin A (1) is reported. Key to the strategy is a Rh-catalyzed [4 + 3] cycloaddition reaction between furan 10 and diazo ester 11 that, following an intramolecular aldol condensation, produces the tricyclic scaffold of englerin. This strategy also provides a rapid, efficient, and stereoselective access to the biologically significant core motif of the guaiane sesquiterpenes.