4.7 Article

Expeditious Construction of the DEF Ring System of Thiersinine B

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 75, Issue 18, Pages 6286-6289

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo101258f

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Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan [22380064]
  2. Grants-in-Aid for Scientific Research [22380064] Funding Source: KAKEN

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Construction of a DEF ring model of thiersinine B has been achieved from a Wieland-Miescher ketone derivative by a five-step sequence featuring a one-pot regioselective alpha-allylation of the starting alpha,beta-unsaturated ketone via the Claisen rearrangement and a double dihydroxylation of a dienone intermediate.

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