Total synthesis of steenkrotins A and B, natural products with antimalarial activity

Several reliable and versatile strategies for the facile total synthesis of antiplasmodial active natural products steenkrotins A and B were proposed. The [A,B,C]tricyclic skeleton was envisioned to be constructed through metal-catalyzed (reductive) Heck- or radical cascades, nitrile oxide mediated 1,3-dipolar cycloadditions or Diels Alder reactions. With the subsequent [D,E] ring-formation based on cyclopropanations or epoxide-opening/ketalization cascades, steenkrotin A could be accessed in a short and concise manner. Meanwhile, the total synthesis of steenkrotin B could be realized through acid- or cobalt catalyzed hydroperoxidation followed by ketalization from a common intermediate. On the other hand, the biomimetic conversion of steenkrotin A to steenkrotin B will also be investigated.

Basic Science

Jan 2015 — Dec 2018

$129,661

China