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Total Synthesis of Ritterazine B

preprint
revised on 04.02.2021, 15:08 and posted on 05.02.2021, 06:30 by Yasuaki Nakayama, Michael Maser, Tatsuya Okita, Anton V. Dubrovskiy, Taryn L. Campbell, Sarah Reisman
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.

Funding

American Cancer Society

History

Email Address of Submitting Author

mmaser@caltech.edu

Institution

California Institute of Technology

Country

United States

ORCID For Submitting Author

0000-0001-7895-7804

Declaration of Conflict of Interest

N/A

Version Notes

V2: Update funding acknowledgments and revise TOC graphic coloring

Exports