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Published March 24, 2021 | Supplemental Material + Submitted
Journal Article Open

Total Synthesis of Ritterazine B

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.

Additional Information

© 2021 American Chemical Society. Received: February 4, 2021; Published: March 9, 2021. Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. We thank Arthur Han for early studies. Fellowship support was provided by the NSF (M.R.M., Grant No. DGE-1144469), the Japan Society for the Promotion of Science (Y.N.), and Ishihara Sangyo Kaisha, Ltd. (T.O.). S.E.R. is a Heritage Medical Research Institute Investigator and acknowledges financial support from the American Cancer Society. The authors declare no competing financial interest.

Attached Files

Submitted - total-synthesis-of-ritterazine-b.pdf

Supplemental Material - ja1c01372_si_001.pdf

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Additional details

Created:
August 20, 2023
Modified:
October 20, 2023