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Synfacts 2007(6): 0563-0563
DOI: 10.1055/s-2007-968521
DOI: 10.1055/s-2007-968521
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Pleocarpenene
Contributor(s):Philip Kocienski, Thomas SnaddonM. J. Williams, H. L. Deak, M. L. Snapper*
Boston College, Chesnut Hill, USA
Intramolecular Cyclobutadiene Cycloaddition/Cyclopropanation/Thermal Rearrangement: An Effective Strategy for the Asymmetric Syntheses of Pleocarpenene and Pleocarpenone
J. Am. Chem. Soc. 2007, 129: 486-487
Boston College, Chesnut Hill, USA
Intramolecular Cyclobutadiene Cycloaddition/Cyclopropanation/Thermal Rearrangement: An Effective Strategy for the Asymmetric Syntheses of Pleocarpenene and Pleocarpenone
J. Am. Chem. Soc. 2007, 129: 486-487
Further Information
Publication History
Publication Date:
23 May 2007 (online)
Key words
iron-cyclobutadiene complex - Corey oxazaborolidine - cross-metathesis - ring fragmentation
Significance
Pleocarpenene is a guaiane natural product. Snapper and co-workers used (1) an intramolecular cyclobutadiene cycloaddition reaction and (2) a thermal ring fragmentation reaction en route to the 5-7-fused ring system.
Comment
Asymmetric reduction of iron-cyclobutadiene complex C using the Corey oxazaborolidine gave enantioenriched E that underwent cross-metathesis giving G. Subsequent oxidation with cerium ammonium nitrate (CAN) gave H as the major diastereoisomer. Later, thermolysis of J in the presence of DBU afforded L as the product of ring fragmentation.