Asymmetric Synthesis of (−)-6-Desmethyl-Fluvirucinine A1 via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions
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
Affiliations
Hyunyoung Moon
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
Hojong Yoon
College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea
Changjin Lim
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
Jaebong Jang
College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea
Jong-Jae Yi
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
Jae Kyun Lee
Center for Neuro-Medicine, Korea Institute of Science and Technology (KIST), Seoul 02792, Korea
Jeeyeon Lee
College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea
Younghwa Na
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
Woo Sung Son
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
Seok-Ho Kim
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
Young-Ger Suh
Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea
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.
