Catalytic enantioselective synthesis of naturally occurring butenolides via hetero-allylic alkylation and ring closing metathesis.
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.
Stratingh Institute for Chemistry, University of Groningen, Groningen, The Netherlands.
Bin
B
Mao
Koen
K
Geurts
Martín
M
Fañanás-Mastral
Anthoni W
AW
van Zijl
Stephen P
SP
Fletcher
Adriaan J
AJ
Minnaard
Ben L
BL
Feringa
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000478:Alkylation; D000498:Allyl Compounds / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000498:Allyl Compounds; D001688:Biological Products; D005663:Furans; C456480:nephrosteranic acid; C428504:roccellaric acid; C004511:butenolide; D015107:4-Butyrolactone