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Synthetic studies directed towards epothilone A: Enantioselective synthesis of a C7  C15 carboxaldehyde segment

✍ Scribed by Panicker Bijoy; Mitchell A. Avery

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
183 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

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-camphorsultam 19 afforded the elaborated acylsultam 20 which was reduced and reoxidized to furnish a protected chiral aldehyde 6 suitable for aldol condensation, representing the C7-C15 portion of epothiione A.

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