Published March 24, 2021
| Supplemental Material + Submitted
Journal Article
Open
Total Synthesis of Ritterazine B
Chicago
An error occurred while generating the citation.
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
Files
total-synthesis-of-ritterazine-b.pdf
Files
(34.0 MB)
| Name | Size | Download all |
|---|---|---|
|
md5:3b0931aed8cea1e70741f90b160c113e
|
2.1 MB | Preview Download |
|
md5:081458a1535af9497ef80f171e918bdf
|
31.9 MB | Preview Download |
Additional details
- Eprint ID
- 107875
- Resolver ID
- CaltechAUTHORS:20210202-123615131
- NSF Graduate Research Fellowship
- DGE-1144469
- Japan Society for the Promotion of Science (JSPS)
- Ishihara Sangyo Kaisha, Ltd.
- Heritage Medical Research Institute
- American Cancer Society
- Created
-
2021-02-02Created from EPrint's datestamp field
- Updated
-
2023-06-01Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute