Stereoselection in the prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral.
[reaction: see text] The condensation of allylic diols with unsymmetrical ketones proceeds with high stereoselection to form 2,2-disubstituted 4-acyltetrahydrofurans when the alpha-substituents of the ketone differ substantially in size. A Prins-pinacol condensation of this type is the central strategic step in an enantioselective synthesis of (-)-citreoviral.
Hanaki
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N
Department of Chemistry, University of California, Irvine 92697-2025, USA.
Link
J T
JT
MacMillan
D W
DW
Overman
L E
LE
Trankle
W G
WG
Wurster
J A
JA
D001313:Aurovertins / Q000138:chemical synthesis*; D005663:Furans / Q000138:chemical synthesis*; D009183:Mycotoxins / Q000138:chemical synthesis; D009498:Neurotoxins / Q000138:chemical synthesis; D013237:Stereoisomerism
D001313:Aurovertins; D005663:Furans; D009183:Mycotoxins; D009498:Neurotoxins; C014416:citreoviridin