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A convenient synthesis of enantiopure (4aS,7aR)-1,4,4a,7a-tetrahydrocyclopenta[c]pyran-3,7-dione

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The title compound, as the new chiral building block for bioactive cyclopentenones, was prepared in 8 steps with 15% overall yield. The key steps involve selective homologation in intermediate [(1S,2R,5R)-5-trimethysilylcyclopent-3-ene-… Click to show full abstract

The title compound, as the new chiral building block for bioactive cyclopentenones, was prepared in 8 steps with 15% overall yield. The key steps involve selective homologation in intermediate [(1S,2R,5R)-5-trimethysilylcyclopent-3-ene- 1,2-diyl]dimethanol by regioselective silylation followed by oxidation and the Wittig reaction.

Keywords: 7ar tetrahydrocyclopenta; convenient synthesis; enantiopure 4as; synthesis enantiopure; tetrahydrocyclopenta pyran; 4as 7ar

Journal Title: Mendeleev Communications
Year Published: 2020

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