Journal
ORGANIC LETTERS
Volume 11, Issue 14, Pages 3124-3127Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900980s
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Funding
- National Institute of General Medical Studies [R01-GM076192]
- National Science Foundation [CHE-0313736, CHE-9974801, CHE-9708640]
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Cross metathesis of the acrolein-derived phosphono allylic carbonate and hydroxy alkenes using second generation Grubbs catalyst and copper(I) iodide gave the substituted phosphonates in good yield. Stereospecific palladium(0)-catalyzed cyclization gave tetrahydrofuran and tetrahydropyran vinyl phosphonates. Regioselective Wacker oxidation of the vinyl phosphonate gave the beta-keto phosphonate, which underwent HWE reaction with benzaldehyde to yield the unsaturated ketone. The utility of the cross metathesis/cyclization protocol was further demonstrated by a formal synthesis of centrolobine.
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