| Autor: |
Liang Xiao-tian, Guo Ji-yu, Liu Rui‐Wu, Yin Da-li |
| Rok vydání: |
2010 |
| Předmět: |
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| Zdroj: |
Chinese Journal of Chemistry. 18:236-246 |
| ISSN: |
1001-604X |
| DOI: |
10.1002/cjoc.20000180219 |
| Popis: |
An oxetane ring can be constructed from 5 α-acyloxy-Δ4(20)-taxoids. The facile intramolecular acyl migration from 5- to 20-position under slightly basic conditions enabled the construction of the oxetane ring in a convenient short cut, whereas the acyl migration from 2- to 20-position left the 2-hydroxyl accessible to a later benzoylation. An unexpected five-membered 4-0, 20-0 sulfite ring was formed in the attempted construction of the oxetane ring with 5α-triflate as a leaving group. After the construction of the oxetane ring, treatment with strong base LiHMDS and acetyl chloride gave the expected 4-0-acetate while treatment with acetic anhydride and DMAP gave a 4-0-acetoacetate. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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