ol100521v_si_001.pdf (1.69 MB)

First Total Synthesis and Structural Confirmation of Fluvirucinine A2 via an Iterative Ring Expansion Strategy

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journal contribution
posted on 07.05.2010, 00:00 by 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
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.