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Synfacts 2007(6): 0563-0563  
DOI: 10.1055/s-2007-968521
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pleocarpenene

Rezensent(en):Philip Kocienski, Thomas Snaddon
M. 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  
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Publikationsdatum:
23. Mai 2007 (online)

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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.

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