期刊
ORGANIC LETTERS
卷 17, 期 11, 页码 2574-2577出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01174
关键词
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资金
- JSPS [26288018]
- Grants-in-Aid for Scientific Research [26288018, 15K05436] Funding Source: KAKEN
A formal synthesis of the antitumor diterpenoid paclitaxel (Taxol) is described. The ABC ring of paclitaxel, synthesized starting from 1,3-cyclohexanedione and tri-O-acetyl-d-glucal by SmI2-mediated cyclization as the key transformation, was successfully converted to Takahashis tetracyclic oxetane intermediate. A double Chugaev reaction was employed for introduction of the strained bridgehead olefin, and stereoselective formation of the oxetane ring afforded the known synthetic intermediate, completing the formal synthesis of paclitaxel.
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