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Natural Product Chemistry Lab
Department of Applied Chemistry Faculty of Engineering, Osaka Institute of Technology
Syntheses of (−)-Tripterifordin and (−)-Neotripterifordin from Stevioside
![Syntheses of (−)-Tripterifordin and (−)-Neotripterifordin from Stevioside](https://static.wixstatic.com/media/4b21d2_baa71dfcf3674c37bc49e8c9f84246bf~mv2.jpg/v1/fill/w_680,h_657,al_c,q_85,usm_0.66_1.00_0.01,enc_auto/JOC2021_edited.jpg)
Short syntheses of (−)-tripterifordin and (−)-neotripterifordin, potent inhibitors of HIV replication, from stevioside, a natural sweetener used worldwide, are reported. 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.
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