Convergent route to the purpuromycin bisphenolic spiroketal: hydrogen bonding control of spiroketalization stereochemistry |
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Authors: | Stephen P. Waters |
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Affiliation: | Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, Philadelphia, PA 19104-6323, United States |
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Abstract: | A mild and efficient [3+2] nitrile oxide/olefin cycloaddition provided a rapid and convergent entry into precursors of bisphenolic spiroketals, a structural type unique to the rubromycin family of natural products. In addition, implementation of the premise that a hydrogen bond from the C4-OH controls the stereochemistry of the purpuromycin core resulted in moderate diastereocontrol in the spiroketalization. Spectroscopic and X-ray data of these systems have provided the first assignment of the relative configuration of purpuromycin. |
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