10.1021/ja055301t.s001
Akiyoshi Kuramochi
Akiyoshi
Kuramochi
Hiroyuki Usuda
Hiroyuki
Usuda
Kenzo Yamatsugu
Kenzo
Yamatsugu
Motomu Kanai
Motomu
Kanai
Masakatsu Shibasaki
Masakatsu
Shibasaki
Total Synthesis of (±)-Garsubellin A
American Chemical Society
2005
enantioselectivity
Koga
Claisen
stereoselective
aldol reaction
prenyl
stereoelective
cyclohexenone
neurotrophic compound
sterically
choline
allyl group
enantioselective alkylation
synthesis
ee
Garsubellin
formation
oxidative
acetaldehyde
enantioenriched
Total Synthesis
garsubellin
rearrangement
metathesi
2005-10-19 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Total_Synthesis_of_Garsubellin_A/3262234
The first total synthesis of garsubellin A, a neurotrophic compound with potent choline acetyltransferase-inducing activity, is described. Keys for success were (1) stereoselective intermolecular aldol reaction at the C-4 position with acetaldehyde, (2) stereoelective Claisen rearrangement to introduce an allyl group to the most sterically crowded position at C-6, (3) ring-closing metathesis to construct the B-ring, and (4) Wacker-type oxidative C-ring formation. This synthetic route can be extended to an asymmetric synthesis of garsubellin A using the Koga catalytic enantioselective alkylation, which produced enantioenriched α-prenyl cyclohexenone with excellent enantioselectivity (95% ee).