Abstract
An oxetane ring can be constructed from 5α-acyloxy-Δ(4(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-O, 20-O 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-O-acetate while treatment with acetic anhydride and DMAP gave a 4-O-acetoacetate.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 236-246 |
| Number of pages | 11 |
| Journal | Chinese Journal of Chemistry |
| Volume | 18 |
| Issue number | 2 |
| State | Published - 2000 |
| Externally published | Yes |
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Keywords
- 20-O-sulfite ring
- Five-membered 4-O
- Intramolecular acyl migration
- Oxetane ring
- Taxoids
- Unusual acylation
ASJC Scopus subject areas
- Chemistry(all)
Cite this
A facile approach for the construction of the oxetane ring from 5α-acyloxy-Δ(4(20))-taxoids. / Liu, Ruiwu; Yin, D. L.; Guo, J. Y.; Liang, X. T.
In: Chinese Journal of Chemistry, Vol. 18, No. 2, 2000, p. 236-246.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - A facile approach for the construction of the oxetane ring from 5α-acyloxy-Δ(4(20))-taxoids
AU - Liu, Ruiwu
AU - Yin, D. L.
AU - Guo, J. Y.
AU - Liang, X. T.
PY - 2000
Y1 - 2000
N2 - An oxetane ring can be constructed from 5α-acyloxy-Δ(4(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-O, 20-O 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-O-acetate while treatment with acetic anhydride and DMAP gave a 4-O-acetoacetate.
AB - An oxetane ring can be constructed from 5α-acyloxy-Δ(4(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-O, 20-O 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-O-acetate while treatment with acetic anhydride and DMAP gave a 4-O-acetoacetate.
KW - 20-O-sulfite ring
KW - Five-membered 4-O
KW - Intramolecular acyl migration
KW - Oxetane ring
KW - Taxoids
KW - Unusual acylation
UR - http://www.scopus.com/inward/record.url?scp=0033833189&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0033833189&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:0033833189
VL - 18
SP - 236
EP - 246
JO - Chinese Journal of Chemistry
JF - Chinese Journal of Chemistry
SN - 1001-604X
IS - 2
ER -