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Asymmetric Synthesis of (-)-6-Desmethyl-Fluvirucinine A1 via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions.
Moon, Hyunyoung; Yoon, Hojong; Lim, Changjin; Jang, Jaebong; Yi, Jong-Jae; Lee, Jae Kyun; Lee, Jeeyeon; Na, Younghwa; Son, Woo Sung; Kim, Seok-Ho; Suh, Young-Ger.
Affiliation
  • Moon H; Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea. hyunyoungmoon@gmail.com.
  • Yoon H; College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea. hyunyoungmoon@gmail.com.
  • Lim C; College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea. hojong_yoon@g.harvard.edu.
  • Jang J; Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea. koryoi0709@gmail.com.
  • Yi JJ; College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea. koryoi0709@gmail.com.
  • Lee JK; College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea. jaebong.jang@gmail.com.
  • Lee J; Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea. nmryi222@gmail.com.
  • Na Y; Center for Neuro-Medicine, Korea Institute of Science and Technology (KIST), Seoul 02792, Korea. j9601@kist.re.kr.
  • Son WS; College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Korea. jyleeut@snu.ac.kr.
  • Kim SH; Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea. yna7315@cha.ac.kr.
  • Suh YG; Department of Pharmacy, College of Pharmacy and Institute of Pharmaceutical Sciences, CHA University, 120 Haeryong-ro, Pocheon 11160, Gyeonggi-do, Korea. wson@cha.ac.kr.
Molecules ; 23(9)2018 Sep 14.
Article in En | MEDLINE | ID: mdl-30223428
ABSTRACT
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.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Lactams Language: En Journal: Molecules Journal subject: BIOLOGIA Year: 2018 Document type: Article

Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Lactams Language: En Journal: Molecules Journal subject: BIOLOGIA Year: 2018 Document type: Article