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A facile approach for the construction of the oxetane ring from 5α‐acyloxy‐△ 4(20) ‐taxoids
Author(s) -
RuiWu Liu,
DaLi Yin,
JiYu Guo,
XiaoTian Liang
Publication year - 2000
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20000180219
Subject(s) - oxetane , chemistry , ring (chemistry) , acetic anhydride , trifluoromethanesulfonate , epoxide , intramolecular force , medicinal chemistry , organic chemistry , catalysis
An oxetane ring can be constructed from 5 α‐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‐ 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.