Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.

Bin Mao, Koen Geurts, Martín Fañanás-Mastral, Anthoni W van Zijl, Stephen P Fletcher, Adriaan J Minnaard, Ben L Feringa

Index: Org. Lett. 13(5) , 948-51, (2011)

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Abstract

An efficient catalytic asymmetric synthesis of chiral γ-butenolides was developed based on the hetero-allylic asymmetric alkylation (h-AAA) in combination with ring closing metathesis (RCM). The synthetic potential of the h-AAA-RCM protocol was illustrated with the facile synthesis of (-)-whiskey lactone, (-)-cognac lactone, (-)-nephrosteranic acid, and (-)-roccellaric acid.