Abstract
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
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