title: A stereo-controlled access to functionalized macrolactams via an aza-Claisen rearrangement.
abstract: A novel and stereo-controlled method for the preparation of functionalized macrolactams was developed. The process involves stereoselective enol ether formation, followed by an azacyclic ring expansion via an aza-Claisen rearrangement. Herewith, we describe a systematic investigation of an aza-Claisen rearrangement-induced ring expansion of azacycles prepared by appending E/Z-enol ethers to the medium-sized lactams as well as the stereochemical outcome. In addition, the strategy was successfully applied to the total synthesis of fluvirucinine A(1) and 3-epi-fluvirucinine A(1). This method offers an attractive alternative to the intramolecular amide-aldol reaction for the elaboration of β-alkoxy-α-substituted motifs.
authors: College of Pharmacy, Seoul National University, Gwanakro 599, Gwanak-gu, Seoul 151-742, Korea. ygsuh@snu.ac.kr
authors: Young-Ger
authors: YG
authors: Suh
authors: Yong-Sil
authors: YS
authors: Lee
authors: Seok-Ho
authors: SH
authors: Kim
authors: Jae-Kyung
authors: JK
authors: Jung
authors: Hwayoung
authors: H
authors: Yun
authors: Jaebong
authors: J
authors: Jang
authors: Nam-Jung
authors: NJ
authors: Kim
authors: Jong-Wha
authors: JW
authors: Jung
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D047029:Lactams, Macrocyclic / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001372:Aza Compounds; D047029:Lactams, Macrocyclic