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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;
- ... Kim, Seok-Ho;
- 외 5명
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5초록
The versatile synthesis of (-)-6-desmethyl-fluvirucinine A(1) 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.
키워드
fluvirucinine; aza-Claisen rearrangement; amidoalkylation; INFLUENZA-A VIRUS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; AZA-CLAISEN REARRANGEMENT; N,O-ACETAL TMS ETHER; ANTHELMINTIC MACROLACTAMS; VERSATILE CONVERSION; SCH 38516; FLUVIRUCIN-B2; ALKALOIDS; AGLYCON
- 제목
- Asymmetric Synthesis of (-)-6-Desmethyl-Fluvirucinine A1 via Conformationally-Controlled Diastereoselective Lactam-Ring Expansions
- 저자
- 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
- 발행일
- 2018-09
- 유형
- Article
- 저널명
- Molecules
- 권
- 23
- 호
- 9
- 언어
- ENG
- 출판사
- MDPI
- 발행국가
- 스위스
- ISSN
- E 1420-3049