4.7 Article

Total synthesis of (-)-amathaspiramide A via a one-pot aldol addition/transamidification reaction

Journal

ORGANIC CHEMISTRY FRONTIERS
Volume 9, Issue 11, Pages 3045-3049

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2qo00032f

Keywords

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Funding

  1. National Natural Science Foundation of China [21871284, 91956113]
  2. Shanghai Municipal Committee of Science and Technology [22ZR1458900, 21ZR1482100, 20XD1423400]
  3. Shanghai Municipal Education Commission [2019-01-07-00-10-E00072]
  4. Shanghai Frontiers Science Center for Traditional Chinese Medicine Chemical Biology

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The total synthesis of (-)-amathaspiramide A was achieved through the efficient construction of a chiral aza-spirobicyclic core using the aldol addition/transamidification cascade. The scope of the efficient construction methodology was investigated, and configuration adjustment via an asymmetric protonation process was identified as a vital step to obtain the correct stereochemistry.
The total synthesis of (-)-amathaspiramide A was accomplished through the efficient construction of a chiral aza-spirobicyclic core using the aldol addition/transamidification cascade. The scope of the efficient construction methodology was investigated. Configuration adjustment via an asymmetric protonation process was applied as a vital step to obtain the right stereochemistry.

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