期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 3, 页码 1606-1613出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02916
关键词
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资金
- JSPS KAKENHI [JP17K07779]
- Grants-in-Aid for Scientific Research [17K07779] Funding Source: KAKEN
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.
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