Publications (2)9.01 Total impact
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Article: Synthesis of simplified tedanolide analogues--connecting tedanolide to myriaporone and gephyronic acid.
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ABSTRACT: Southern belles! Simplified analogues of tedanolide, a natural product with picomolar activity against a range of tumor cell lines, were synthesized and evaluated for potency in mammalian cancer cells. The truncated analogues were found to retain significant activity in vitro (23 μmol mL(-1) for the example shown) compared with the parent compound tedanolide (0.33 nmol mL(-1)), and represent potential leads for the development of novel anticancer agents.ChemMedChem 03/2012; 7(5):771-5. · 3.15 Impact Factor -
Article: A Kiyooka aldol approach for the synthesis of the C(14)-C(23) segment of the diastereomeric analog of tedanolide C.
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ABSTRACT: The challenging synthesis of a quaternary center within the highly oxygenated setting of tedanolide C can be performed via a Kiyooka aldol reaction. Here, the diastereomeric analog of tedanolide C with the configurations between C10 and C20 opposite compared to the proposed structure was chosen as the synthetic target. The tetra-substituted silyl ketene acetal provides the southern hemisphere of tedanolide C in useful selectivities, and the absolute configuration of the newly generated quaternary center was determined by NOE experiments of the corresponding acetonide.Organic Letters 11/2011; 13(22):6038-41. · 5.86 Impact Factor
