Syntheses of (−)-Tripterifordin and (−)-Neotripterifordin from Stevioside,The Journal of Organic Chemistry

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Syntheses of (−)-Tripterifordin and (−)-Neotripterifordin from Stevioside
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-01-12 00:00:00 , DOI: 10.1021/acs.joc.7b02916
Shoji Kobayashi ₁ , Keisuke Shibukawa ₁ , Yoshiki Hamada ₁ , Takuma Kuruma ₁ , Asako Kawabata ₁ , Araki Masuyama ₁

Affiliation

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.

中文翻译：

甜菊糖中（-）-曲霉菌素和（-）-新三萜素的合成

我们报道了甜菊糖（全球使用的天然甜味剂）的短效合成（-）-雷公藤素和（-）-新雷公藤素，它们是HIV复制的有效抑制剂。关键的转变是通过叔氯的形成在C13还原，以及随后的三步内酯化，包括通过C19醇的光反应在C20进行选择性碘化。从甜菊糖中分别以9和11个步骤（带有5-7个分离步骤）可靠地获得了标题化合物。此外，相关的含内酯的ent- kaurenes，doianoterpenes A和B，和两个天然产品合成的。

更新日期：2018-01-12

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