First Total Synthesis and Structural Confirmation of Fluvirucinine A2 via an Iterative Ring Expansion Strategy
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- 作者：Yong-Sil Lee ; Jong-Wha Jung ; Seok-Ho Kim ; Jae-Kyung Jung ; Seung-Mann Paek ; Nam-Jung Kim ; Dong-Jo Chang ; Jeeyeon Lee ; Young-Ger Suh
- 刊名：Organic Letters
- 出版年：2010
- 出版时间：May 7, 2010
- 年：2010
- 卷：12
- 期：9
- 页码：2040-2043
- 全文大小：210K
- 年卷期：v.12,no.9(May 7, 2010)
- ISSN：1523-7052
文摘
The first asymmetric total synthesis of fluvirucinine A2 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 A2 has been completely elucidated by our total synthesis.