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.
[reaction: see text] 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 Co(2)(CO)(8), proceeded in a highly regio- and stereoselective fashion.
Smith
Amos B
AB
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
Fox
Richard J
RJ
D000143:Acids / Q000737:chemistry*; D000617:Aminoglycosides / Q000138:chemical synthesis*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000143:Acids; D000617:Aminoglycosides; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004852:Epoxy Compounds; C493209:dioxabicyclo(3.2.1)octane; C051799:sorangicin A