%0 Journal Article %A Lee, Yong-Sil %A Jung, Jong-Wha %A Kim, Seok-Ho %A Jung, Jae-Kyung %A Paek, Seung-Mann %A Kim, Nam-Jung %A Chang, Dong-Jo %A Lee, Jeeyeon %A Suh, Young-Ger %D 2010 %T First Total Synthesis and Structural Confirmation of Fluvirucinine A2 via an Iterative Ring Expansion Strategy %U https://acs.figshare.com/articles/journal_contribution/First_Total_Synthesis_and_Structural_Confirmation_of_Fluvirucinine_A_sub_2_sub_via_an_Iterative_Ring_Expansion_Strategy/2771275 %R 10.1021/ol100521v.s001 %2 https://acs.figshare.com/ndownloader/files/4465690 %K Iterative Ring Expansion Strategy %K synthesis %K iterative lactam ring expansion %K stereogenic centers %K fluvirucinine %X 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. %I ACS Publications