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
Citations

WEB OF SCIENCE

28
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SCOPUS

29

초록

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 VIRUSN,O-ACETAL TMS ETHERCLAISEN REARRANGEMENTVERSATILE CONVERSIONSCH 38516MACROLACTAMAMIDESREDUCTIONAGLYCONA(1)
제목
First Total Synthesis and Structural Confirmation of Fluvirucinine A2 via an Iterative Ring Expansion Strategy
저자
Lee, Yong-SilJung, Jong-WhaKim, Seok-HoJung, Jae-KyungPaek, Seung-MannKim, Nam-JungChang, Dong-JoLee, JeeyeonSuh, Young-Ger
DOI
10.1021/ol100521v
발행일
2010-05-07
유형
Article
저널명
Organic Letters
12
9
페이지
2040 ~ 2043