Abstract
AbstractAn 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.
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