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Total syntheses of (+)- and (−)-Crinane via Pd(0)-Catalyzed deacylative allylation

Abstract An efficient Pd(0)-catalyzed deacylative allylation (DaA) of enolcarbonates (pro-nucleophile) prepared from 2-arylcyclohexanones sharing acyl functionality at C2-position with readily available allylic alcohols (pro-electrophiles) by employing Pd(0)-catalysis under mild reaction… Click to show full abstract

Abstract An efficient Pd(0)-catalyzed deacylative allylation (DaA) of enolcarbonates (pro-nucleophile) prepared from 2-arylcyclohexanones sharing acyl functionality at C2-position with readily available allylic alcohols (pro-electrophiles) by employing Pd(0)-catalysis under mild reaction conditions. The methodology can be extended for deacylative benzylations (DaB) of enolcarbonates of 2-arylcyclohexanones. As an application of our methodology, we have shown asymmetric total synthesis of Amaryllidaceae alkaloids, (+)- and (−)-crinane.

Keywords: syntheses crinane; methodology; catalyzed deacylative; total syntheses; deacylative allylation

Journal Title: Tetrahedron
Year Published: 2021

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