Role of conformational effects on the regioselectivity of macrocyclic INOC reactions: two new asymmetric total syntheses of (+)-brefeldin A.
We have gained some insight into the role of conformational effects on the regioselectivity of the macrocyclic intramolecular nitrile oxide cycloaddition observed in our (+)-brefeldin A synthesis. During the course of this regiochemical study, we have developed two novel stereoselective and regioselective schemes for total synthesis of (+)-brefeldin A (i.e. intramolecular nitrile oxide cycloaddition-isomerization and intermolecular nitrile oxide cycloaddition-ring closing metathesis strategies).
Kim
Deukjoon
D
Research Institute of Pharmaceutical Sciences, College of Pharmacy, Seoul National University, San 56-1, Shillim-Dong, Kwanak-Ku, Seoul 151-742, Korea. deukjoon@plaza.snu.ac.kr
Lee
Jongkook
J
Shim
Phil Jong
PJ
Lim
Joong Inn
JI
Doi
Takayuki
T
Kim
Sanghee
S
D020126:Brefeldin A / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013057:Spectrum Analysis
D020126:Brefeldin A