4.3 Article

Total Syntheses of (+)-Sesamin and (+)-Sesaminol

Journal

CHEMISTRY LETTERS
Volume 43, Issue 10, Pages 1572-1574

Publisher

CHEMICAL SOC JAPAN
DOI: 10.1246/cl.140613

Keywords

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Funding

  1. Uehara Memorial Foundation
  2. MEXT/JSPS KAKENHI [23390007, 26860013]
  3. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan [12045232, 24105530]
  4. Ministry of Education, Culture, Sports, Science and Technology
  5. Grants-in-Aid for Scientific Research [24105530, 26860013, 23390007, 26102736] Funding Source: KAKEN

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Total syntheses of (+)-sesamin (1a) and (+)-sesaminol (1b), which are major components of sesame lignans derived from Sesamum indicum, were accomplished in a highly stereo-controlled manner. Key steps include an L-proline-catalyzed cross-aldol reaction, which was accelerated with the aid of bifunctional urea 7, and the construction of a furofuran lignan skeleton through a quinomethide intermediate.

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