First total synthesis and structural confirmation of fluvirucinine A2 via an iterative ring expansion strategy.

نویسندگان

  • 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
چکیده

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.

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عنوان ژورنال:
  • Organic letters

دوره 12 9  شماره 

صفحات  -

تاریخ انتشار 2010