139122-81-9Relevant articles and documents
Syntheses of (-)-Tripterifordin and (-)-Neotripterifordin from Stevioside
Kobayashi, Shoji,Shibukawa, Keisuke,Hamada, Yoshiki,Kuruma, Takuma,Kawabata, Asako,Masuyama, Araki
, p. 1606 - 1613 (2018)
We report short syntheses of (-)-tripterifordin and (-)-neotripterifordin, potent inhibitors of HIV replication, from stevioside, a natural sweetener used worldwide. The key transformations are reduction at C13 through the formation of a tertiary chloride and subsequent three-step lactonization including a selective iodination at C20 by the photoreaction of the C19-alcohol. The title compounds were reliably obtained from stevioside in 9 and 11 steps (with 5-7 isolation steps), respectively. Additionally, the related lactone-containing ent-kaurenes, doianoterpenes A and B, and two more natural products were synthesized.