4.8 Article

Total Synthesis of Mollanol A

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 144, Issue 33, Pages 15033-15037

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.2c06981

Keywords

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Funding

  1. Lanzhou University
  2. National Natural Science Foundation of China [21901094, 22071089]
  3. Fundamental Research Funds for the Central Universities [zujbky-2019-49, zujbky-2020-ct01]

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This study reports the first total synthesis method for mollanol A, which involves a 15-step synthesis process using a convergent strategy to construct its unique molecular structure.
Mollanol A is the first isolated member of the mollane-type grayanoids which possesses an unprecedented C-nor-D-homograyanane carbon skeleton and an 5,8-epoxide. Due to its transcriptional activation effects on the Xbp1 upstream promoters in different cell types, it has a potential therapeutic effect on inflammatory bowel disease. Here we report the first total synthesis of mollanol A, which constitutes a 15-step synthesis from commercially available materials via a convergent strategy. The synthesis involves an InCl3-catalyzed Conia-ene cyclization reaction to construct the bicyclo[3.2.1]octane moiety and a vinylogous aldol reaction/intramolecular oxa-Michael addition sequence to rapidly assemble the oxa-bicyclo[3.2.1] core.

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