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Total Synthesis of Ritterazine B.
J Am Chem Soc
March 2021
The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, United States.
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.
View Article and Find Full Text PDFAllene-alkyne cross-coupling for stereoselective synthesis of substituted 1,4-dienes and cross-conjugated trienes.
Tetrahedron
April 2008
Department of Chemistry, Yale Univeristy, New Haven, Connecticut 06520-8107.
Titanium-mediated cross-coupling of allenic alcohols with alkynes has been investigated. Divergent reaction pathways were discovered that provide either stereodefined 1,4-dienes or substituted cross-conjugated trienes. In short, allene substitution plays a critical role in the determination of reaction pathway.
View Article and Find Full Text PDFDivergent titanium-mediated allylations with modulation by nickel or palladium.
Angew Chem Int Ed Engl
November 2008
Department of Organic Chemistry, Faculty of Sciences, University of Granada, Spain.
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