- Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.
Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.
Organic letters (2011-01-28)
Bin Mao, Koen Geurts, Martín Fañanás-Mastral, Anthoni W van Zijl, Stephen P Fletcher, Adriaan J Minnaard, Ben L Feringa
PMID21268603
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.
MATERIALS