A stereo-controlled access to functionalized macrolactams via an aza-Claisen rearrangement

作者:Suh Young Ger*; Lee Yong Sil; Kim Seok Ho; Jung Jae Kyung; Yun Hwayoung; Jang Jaebong; Kim Nam Jung; Jung Jong Wha
来源:ORGANIC %26 BIOMOLECULAR CHEMISTRY, 2012, 10(3): 561-568.
DOI:10.1039/c1ob06733h

摘要

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 beta-alkoxy-alpha-substituted motifs.

  • 出版日期2012