- Syntheses of (-)-Tripterifordin and (-)-Neotripterifordin from Stevioside
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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.
- Kobayashi, Shoji,Shibukawa, Keisuke,Hamada, Yoshiki,Kuruma, Takuma,Kawabata, Asako,Masuyama, Araki
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- Diterpenoid Total Synthesis, XXX. Synthesis of the Racemic Form of Tripterifordin, a Novel Anti-HIV Diterpene Lactone from Tripterygium wilfordii
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The pentacyclic diterpene ketone (+/-)-3, which dad been prepared by a total synthesis from naphthalene, was methylenated and hydrated to give (+/-)-tripterifordin , the racemate of a new kaurane-type diterpene lactone with anti-HIV activity recently isolated from the roots of Tripterygium wilfordii. Key Words: HIV / Diterpenes / Kaurane derivatives / Terpenes / Tripterifordin / Tripterygium wilfordii
- Mori, Kenji,Aki, Shinji
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