Total Synthesis of Ritterazine B
Yasuaki Nakayama, Michael Maser, Tatsuya Okita, Anton V. Dubrovskiy, Taryn L. Campbell, Sarah E. Reisman
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.
Topics & Concepts
ChemistryTotal synthesisStereochemistryAlkaloidCombinatorial chemistryAlcoholOrganic chemistryMarine Sponges and Natural ProductsOxidative Organic Chemistry ReactionsTraditional and Medicinal Uses of Annonaceae