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First Total Synthesis and Structural Confirmation of Fluvirucinine A2 via an Iterative Ring Expansion Strategy
- Lee, Yong-Sil;
- Jung, Jong-Wha;
- Kim, Seok-Ho;
- Jung, Jae-Kyung;
- Paek, Seung-Mann;
- 외 4명
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WEB OF SCIENCE
28Citations
SCOPUS
29초록
The first asymmetric total synthesis of fluvirucinine A(2) has been accomplished. A key feature of the synthesis is an iterative lactam ring expansion to provide rapid access to the 14-membered lactam skeleton and three stereogenic centers. The excellent remote control of the three stereogenic centers relied on stereoselective amidoalkylation followed by an amide-enolate-induced aza-Claisen rearrangement. In addition, the structure of fluvirucinine A(2) has been completely elucidated by our total synthesis.
키워드
INFLUENZA-A VIRUS; N,O-ACETAL TMS ETHER; CLAISEN REARRANGEMENT; VERSATILE CONVERSION; SCH 38516; MACROLACTAM; AMIDES; REDUCTION; AGLYCON; A(1)
- 제목
- First Total Synthesis and Structural Confirmation of Fluvirucinine A2 via an Iterative Ring Expansion Strategy
- 저자
- Lee, Yong-Sil; Jung, Jong-Wha; Kim, Seok-Ho; Jung, Jae-Kyung; Paek, Seung-Mann; Kim, Nam-Jung; Chang, Dong-Jo; Lee, Jeeyeon; Suh, Young-Ger
- 발행일
- 2010-05-07
- 유형
- Article
- 저널명
- Organic Letters
- 권
- 12
- 호
- 9
- 페이지
- 2040 ~ 2043