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Synfacts 2007(3): 0258-0258  
DOI: 10.1055/s-2007-968253
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Cyclopentenone-Fused Perhydroperans via Pauson-Khand Reaction

Contributor(s): Victor Snieckus, Kristoffer Månsson
S. Sezer, D. Özdemirhan, E. Şahin, C. Tanyelia*
Middle East Technical University, Ankara, Turkey
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Publication History

Publication Date:
20 February 2007 (online)

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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.