Synthetic studies in the lysocellin family of polyether antibiotics. The total synthesis of ferensimycin B

Autor:	David J. Mathre, David A. Evans, Denise E. Guinn, K. M. Devries, Richard P. Polniaszek
Rok vydání:	1991
Předmět:	chemistry.chemical_classification Stereochemistry Carboxylic acid Absolute configuration Enantioselective synthesis Total synthesis General Chemistry Biochemistry Asymmetric induction Catalysis Stereocenter Colloid and Surface Chemistry chemistry Aldol reaction Chirality (chemistry)
Zdroj:	Journal of the American Chemical Society. 113:7613-7630
ISSN:	1520-5126 0002-7863
Popis:	A convergent asymmetric synthesis of the polyether antibiotic ferensimycin B has been completed. Chiral enolate bond constructions were employed to establish seven of the 16 stereocenters of the subunits 35 and 52, which comprise the C& and CI&3 portions of ferensimycin B. The stereogenic centers at C3, C4, Cg, Clo, CI6, C,,, and CIS were incorporated through internal asymmetric induction, while those at Cm and C1l were established by using asymmetric epoxidation methodology. In this transformation, a vanadium-catalyzed internal epoxidation of a bis-homoallylic alcohol was employed to relay chirality from the C13 to the CI6 oxygen-bearing stereocenter. A final aldol addition reaction on intermediates devoid of protecting groups united the fragments 52 and 35 to provide synthetic ferensimycin B, whose absolute configuration was found to be
Databáze:	OpenAIRE
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