A formal total synthesis of dysidiolide.
[structure] A formal total synthesis of the natural product dysidiolide is described. Starting from a Diels-Alder reaction between an enoate and a Rawal diene, the cyclohexenone 4 was synthesized. A subsequent stereospecific methyl cuprate addition established the desired trans configuration in the cyclohexane 3. Wacker oxidation of the pentenyl side chain to the diketone 17 followed by an intramolecular aldol condensation led to the bicyclic enone 2, a key intermediate in a recently reported synthesis of dysidiolide.
Paczkowski
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Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany.
Maichle-Mössmer
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C
Maier
M E
ME
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D014961:X-Ray Diffraction; D020687:cdc25 Phosphatases / Q000037:antagonists & inhibitors*
D004791:Enzyme Inhibitors; D020687:cdc25 Phosphatases; C121906:dysidiolide; D015107:4-Butyrolactone