10.1021/jo5029166.s001
Huijing Wang
Huijing
Wang
Pei Tang
Pei
Tang
Qilong Zhou
Qilong
Zhou
Dan Zhang
Dan
Zhang
Zhitao Chen
Zhitao
Chen
Hongxiu Huang
Hongxiu
Huang
Yong Qin
Yong
Qin
One-Pot Synthesis of Multisubstituted
Butyrolactonimidates:
Total Synthesis of (−)-Nephrosteranic Acid
American Chemical Society
2015
furan
cascade reaction
usefulness
acid
Butyrolactonimidate
synthesis
Multisubstituted
hydroxylation
Nephrosteranic
intermediate
imidate
Synthesi
butyrolactonimidate
diester
butyrolactone
nephrosteranic
chiral
preparation
AcidMultisubstituted
stereoselective Michael addition
Total
cyclization
2015-03-06 00:00:00
Dataset
https://acs.figshare.com/articles/dataset/One_Pot_Synthesis_of_Multisubstituted_Butyrolactonimidates_Total_Synthesis_of_Nephrosteranic_Acid/2189218
Multisubstituted
chiral butyrolactonimidates have been synthesized
via a one-pot, three-step cascade reaction in which (<i>R</i>)-<i>N</i>-<i>tert</i>-butanesulfinyl imidates
and α,β-unsaturated diesters undergo highly stereoselective
Michael addition, anion-oxidative hydroxylation, and cyclization.
The synthesized butyrolactonimidates are versatile intermediates for
preparation of substituted butyrolactones and furans. The usefulness
of this cascade reaction is demonstrated through the concise total
synthesis of natural product (−)-nephrosteranic acid.