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Synfacts 2007(3): 0258-0258
DOI: 10.1055/s-2007-968253
DOI: 10.1055/s-2007-968253
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Cyclopentenone-Fused Perhydroperans via Pauson-Khand Reaction
S. Sezer, D. Özdemirhan, E. Şahin, C. Tanyelia*
Middle East Technical University, Ankara, Turkey
Further Information
Publication History
Publication Date:
20 February 2007 (online)
Significance
The synthesis of optically active cyclopentenone-fused perhydropyrans, involving key steps of enzymatic resolution of intermediate furanyl propargylic and allylic alcohols, followed by intramolecular Pauson-Khand reactions, is reported. The enzyme PS-C Amano II effects resolution of the substituted homoallylic and homopropargylic alcohols through selective carbinol acylation, with high levels of enantioselectivity.