cheminform abstract: total synthesis of (-)-epothilone a

1997 other bioactive products other bioactive products U 1300 13 - 213 Total Synthesis of (-)-Epothilone A. — Starting with the chiral building blocks (I) and (II) (preparations are described) coupling product (III) is obtained, the important precursor for the key cyclization. With (III) the aggressive strategy of employing the methyl group of the C-1 bound acetoxy function as the nucleophilic component in the macroaldolization is explored. This highly stereoselective macroaldolization results in the formation of the C-3 (S)-alcohol (IV), from which the title compound (V) is prepared in several steps. — (BALOG, A.; MENG, D.; KAMENECKA, T.; BERTINATO, P.; SU, D.-S.; SORENSEN, E. J.; DANISHEFSKY, S. J.; Angew. Chem. 108 (1996) 23-24, 2976-2978; Lab. Bioorg. Chem., Sloan-Kettering Inst. Cancer Res., New York, NY 10021, USA; DE) 1

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Page 1: ChemInform Abstract: Total Synthesis of (-)-Epothilone A

1997 other bioactive products

other bioactive productsU 1300

13 - 213Total Synthesis of (-)-Epothilone A. — Starting with the chiral buildingblocks (I) and (II) (preparations are described) coupling product (III) isobtained, the important precursor for the key cyclization. With (III) theaggressive strategy of employing the methyl group of the C-1 bound acetoxyfunction as the nucleophilic component in the macroaldolization is explored.This highly stereoselective macroaldolization results in the formation of the C-3(S)-alcohol (IV), from which the title compound (V) is prepared in several steps.— (BALOG, A.; MENG, D.; KAMENECKA, T.; BERTINATO, P.; SU, D.-S.;SORENSEN, E. J.; DANISHEFSKY, S. J.; Angew. Chem. 108 (1996) 23-24,2976-2978; Lab. Bioorg. Chem., Sloan-Kettering Inst. Cancer Res., New York,NY 10021, USA; DE)

ChemInform Sheet A4on chemo-, regio-, and stereo-selective reactions. The RefLib database is included with CIRX and provides reactions abstracted from Theilheimer’s Synthetic Methods

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