(+)-Sorangicin A synthetic studies. Construction of the C(1-15) and C(16-29) subtargets |
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Authors: | Smith Amos B Fox Richard J Vanecko John A |
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Institution: | Department of Chemistry, Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, 19104, USA. smithab@sas.upenn.edu |
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Abstract: | structure: see text] Effective stereocontrolled syntheses of subtargets (-)-2 and (-)-4, comprising respectively the C(16-29) and C(1-15) tetrahydropyran and dihydropyran moieties of the potent antibiotic (+)-sorangicin A (1), have been achieved. The cornerstone for the synthesis of (-)-2 involved an aldol tactic exploiting 1,4-induction, followed in turn by an acid-mediated cyclization/ketalization and hydrosilane reduction promoted by TMSOTf, while construction of (-)-4 entailed a stereoselective conjugate addition/alpha-oxygenation sequence. |
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