Aldol condensation reactions of tricarbonyliron complexes. Towards building blocks for the synthesis of carbomycin B/tylosin macrolide antibiotics and fluorinated analogs

Author:

Franck-Neumann Michel,Geoffroy Philippe,Gumery Fabien

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference11 articles.

1. Franck-Neumann, M.; Geoffroy, P.; Gumery, F.; Bissinger, P. (in part) Tetrahedron Lett. 2000, 41, 4213–4217.

2. The building block 1 was obtained from glucose diacetonide in nine steps with an overall yield of 42%, (Pg=Bn7), or 34% (Pg=MOM8). The building block 2 was more tedious to obtain, and was prepared in 11 steps with 28% overall yield (methyl ester, Pg=Bn9) from a 3-C-methyl-d-glucoside which was obtained from d-glucose in 40% overall yield,10 or in 19 steps from glucose diacetonide in 11% overall yield (ethyl ester, Pg=Bn).11 Mixtures of E- and Z-isomers were always obtained.

3. Franck-Neumann, M.; Bissinger, P.; Geoffroy, P. Tetrahedron Lett. 1997, 38, 4469.

4. Slomp Jr., G.; Johnson, J. L. J. Am. Chem. Soc. 1958, 80, 915.

5. Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616.

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