Method for synthesizing epothilones and epothilone analogs
AssigneeState of Oregon acting by and through the State Board of Higher Education on behalf of Oregon State University
InventorsJames David White, Rich Garrett Carter, Kurt Frederick Sundermann
Life of this patent
Estimating the term…
Abstract
A method for making epothilones and epothilone analogs is described, as are novel compounds made by the method. One embodiment of the method was used to synthesize epothilone B by a convergent approach that entailed Wittig coupling of an ylide derived from phosphonium bromide with an aldehyde. The former was prepared from propargyl alcohol by a nine-step pathway which installed both trisubstituted double bonds with clean Z configuration. Macrolactonization of a resulting seco acid provided the following intermediate diene epothilone analog. Selective saturation of the 9,10-olefin and subsequent epoxidation provided epothilone B.
Claims4
A compound according to the formula:
- where R substituents independently are H, lower alkyl, or a protecting group, R1 is
- R2 and R3 independently are H or lower aliphatic groups, R4 substituents independently are selected from the group consisting of lower aliphatic groups, and R5 and R6 independently are H or lower aliphatic.
Dependencies are inferred from the claim text.