Stereoselective synthesis of the C7C21 segment of epothilone A via asymmetric alkoxyallyl- and crotylboration
✍ Scribed by P.Veeraraghavan Ramachandran; Bodhuri Prabhudas; Debarshi Pratihar; J.Subash Chandra; M.Venkat Ram Reddy
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 272 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The synthesis of the C 7 C 21 fragment of epothilone A involving asymmetric alkoxyallyl-and crotylboration using a-pinene-derived reagents is described.
📜 SIMILAR VOLUMES
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.
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
The C( 1)-C(9) segment 3 of the macrolides epothilon A and B 1, two new cytotoxic natural products, has been synthesized in a direct manner. Key steps in the synthesis are a stereoselective aldol reaction of 6 and 7 and a Brown allylation of 9.