Epoxide opening with acetylide for synthesis of epothilone A C7–21 segment
✍ Scribed by Zhi-yu Liu; Chen-zhi Yu; Rui-Fang Wang; Gang Li
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 172 KB
- Volume
- 39
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
A Chiral synthesis ofepothilone A C7-21 segment 2 is described using epoxide opening with acetylide for the construction of the C~2.~.~ cis double bond and a modified Wittig reaction tbr introduction of the thiazole side chain.
📜 SIMILAR VOLUMES
The synthesis of the C 7 C 21 fragment of epothilone A involving asymmetric alkoxyallyl-and crotylboration using a-pinene-derived reagents is described.
Disstereo-andregioselective opening ofa trisubstituted epoxy ketone atthemoresubstituted carbon using sanrarium(II) iodide presents an alternate approach to the C5-C7 afdol moiety with & hydroxyketoframework in the stereoselectivesynthesisof C1-C12 segmentof epothilones.
Enantioselective syntheses of a protected C7-C15 fragment of epothilone A is reported in ten manipulations in good overall yield. An alkynyl-aluminum induced opening of a chiral epoxide followed by reordering of functionality furnished the iodide 18. Chain elongation with N-propionyl-lS-(-)-2,10-cam