Synthetic studies toward 1,2-dioxanes as precursors of potential endoperoxide-containing antimalarials

Tetrahedron Letters

Volumn 50, Issue 41, 2009, Pages 5719-5722

  Gemma, Sandra ^a   Martí, Francesc ^a   Gabellieri, Emanuele ^a   Campiani, Giuseppe ^a   Novellino, Ettore ^a,b   Butini, Stefania ^a  

^a UNIVERSITY OF SIENA   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

1,2 Endoperoxides; Enantioselective synthesis; Isayama reaction; Sharpless epoxidation

Indexed keywords

1,2 DIOXANE DERIVATIVE; 4 BENZYL 3 BUTYRYLOXAZOLIDIN 2 ONE; ALDEHYDE; ANTIMALARIAL AGENT; ARTEMISININ; ENDOPEROXIDE; EPOXIDE; OXAZOLIDINEDIONE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CYCLIZATION; CYCLOADDITION; DRUG MECHANISM; DRUG SYNTHESIS; MALARIA FALCIPARUM; OLEFINATION; PLASMODIUM FALCIPARUM; SHARPLESS EPOXIDATION; SILYLATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 68949183478     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.07.137     Document Type: Article

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35. 2 (11 mg) in 1,2-dichloroethane (5 mL), was stirred under an oxygen atmosphere. To the resulting pink solution, triethylsilane (82 μL, 0.52 mmol) was added, followed by a catalytic amount of t-BuOOH (6 M in nonane). The resulting dark green solution was stirred at 25 °C until the starting material disappeared. Amberlyst-15 (20 mg) was subsequently added to the reaction mixture which was stirred at 25 °C for 3 h. The resin was removed by filtration and the solvent was evaporated to afford a crude product which was purified by flash chromatography (1:2 diethyl ether/petroleum ether) to afford 6a as a colorless oil (75%).
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