Method for synthesizing epothilones and epothilone analogs
US6596875B2 · kind B2 · utility
18Cited by
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30Claims
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Inventors
Key dates
| Filing date | Apr 30, 2001 |
| Grant date | Jul 22, 2003 |
| Priority date | — |
| Expiry date | Apr 30, 2021 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D417/06
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
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.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.