American Chemical Society
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Construction of a C(30−38) Dioxabicyclo[3.2.1]octane Subtarget for (+)-Sorangicin A, Exploiting a Regio- and Stereocontrolled Acid-Catalyzed Epoxide Ring Opening

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journal contribution
posted on 2004-04-29, 00:00 authored by Amos B. Smith, Richard J. Fox
In this paper, we report assembly of the novel dioxabicyclo[3.2.1]octane subtarget (−)-2, comprising the signature structural element of the potent antibiotic (+)-sorangicin A (1). The synthesis was achieved in 15 steps (1.5% overall yield) via a series of acid-catalyzed epoxide ring openings. The first, facilitated by the complex of alkyne (+)-3 with Co2(CO)8, proceeded in a highly regio- and stereoselective fashion.