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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| Authors: | Smith Amos B Fox Richard J |
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| Institution: | Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu |
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| Abstract: | reaction: see text] In this paper, we report assembly of the novel dioxabicyclo3.2.1]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 Co(2)(CO)(8), proceeded in a highly regio- and stereoselective fashion. |
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