title: Role of conformational effects on the regioselectivity of macrocyclic INOC reactions: two new asymmetric total syntheses of (+)-brefeldin A.
abstract: 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).
authors.affiliation: 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
authors.forename: Deukjoon
authors.initials: D
authors.lastname: Kim
authors.forename: Jongkook
authors.initials: J
authors.lastname: Lee
authors.forename: Phil Jong
authors.initials: PJ
authors.lastname: Shim
authors.forename: Joong Inn
authors.initials: JI
authors.lastname: Lim
authors.forename: Takayuki
authors.initials: T
authors.lastname: Doi
authors.forename: Sanghee
authors.initials: S
authors.lastname: Kim
mesh_terms: D020126:Brefeldin A / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013057:Spectrum Analysis
chemical_list: D020126:Brefeldin A