Journal
ORGANIC LETTERS
Volume 12, Issue 9, Pages 2040-2043Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol100521v
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Funding
- Center for Bioactive Molecular Hybrid, Yonsei University
- Ministry of Education, Science and Technology (MEST), the Republic of Korea [2009K001255]
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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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