Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A1 via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions
oleh: Hyunyoung Moon, Hojong Yoon, Changjin Lim, Jaebong Jang, Jong-Jae Yi, Jae Kyun Lee, Jeeyeon Lee, Younghwa Na, Woo Sung Son, Seok-Ho Kim, Young-Ger Suh
| Format: | Article |
|---|---|
| Diterbitkan: | MDPI AG 2018-09-01 |
Deskripsi
The versatile synthesis of (−)-6-desmethyl-fluvirucinine A1 was accomplished at a 24% overall yield through a thirteen-step process from a known vinylpiperidine. The key part involved the elaboration of the distal stereocenters and a macrolactam skeleton via conformationally-induced diastereocontrol and the iterative aza-Claisen rearrangements of lactam precursors.