ISSN:
0947-6539
Keywords:
epothilone
;
oxazoles
;
cyclopropanes
;
metathesis
;
total synthesis
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
For structure-activity relationship studies, two series of epothilone A (1) analogues have been designed and synthesized, one containing an oxazole moiety instead of the thiazole heterocycle and the other containing a spirocyclopropane moiety in place of the gem-dimethyl group at position C-4 (4,4-ethano-epothilones). The olefin metathesis strategy in solution was utilized for the chemical synthesis of these compounds starting with key building blocks 7-9 for the oxazole series (compounds 2, 14-18, 21-26) and building blocks 8, 30, and 31 for the 4,4-ethano series (compounds 3,39-43, 46-51). The convergent strategy towards the designed epothilone A series involved a) an aldol condensation reaction, b) an esterification reaction, c) an olefin metathesis reaction catalyzed by [RuCl2(=CHPh)-(PCy3)2], and d) epoxidation of the macrocycle double bond.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970031211
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