Abstract
The first total synthesis of the cytotoxic alkaloid ritterazine B is reported. The synthesis features a unified approach to both steroid subunits, employing a titanium-mediated propargylation reaction to achieve divergence from a common precursor. Other key steps include gold-catalyzed cycloisomerizations that install both spiroketals and late stage C-H oxidation to incorporate the C7' alcohol.
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Animals
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Catalysis
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Gold / chemistry
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Molecular Conformation
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Phenazines / chemical synthesis*
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Phenazines / chemistry
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Spiro Compounds / chemical synthesis*
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Spiro Compounds / chemistry
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Stereoisomerism
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Steroids / chemical synthesis*
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Steroids / chemistry
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Urochordata / chemistry
Substances
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Antineoplastic Agents
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Phenazines
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Spiro Compounds
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Steroids
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ritterazine B
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Gold