CaltechAUTHORS
  A Caltech Library Service

Total Synthesis of Ritterazine B

Nakayama, Yasuaki and Maser, Michael R. and Okita, Tatsuya and Dubrovskiy, Anton V. and Campbell, Taryn L. and Reisman, Sarah E. (2021) Total Synthesis of Ritterazine B. Journal of the American Chemical Society, 143 (11). pp. 4187-4192. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20210202-123615131

[img] PDF - Submitted Version
Creative Commons Attribution Non-commercial No Derivatives.

2MB
[img] PDF - Supplemental Material
See Usage Policy.

31MB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20210202-123615131

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.1c01372DOIArticle
https://doi.org/10.26434/chemrxiv.13623155.v2DOIDiscussion Paper
https://pubs.acs.org/doi/10.1021/cen-09910-scicon3Featured InC&EN : Synthesis
ORCID:
AuthorORCID
Maser, Michael R.0000-0001-7895-7804
Reisman, Sarah E.0000-0001-8244-9300
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.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
NSF Graduate Research FellowshipDGE-1144469
Japan Society for the Promotion of Science (JSPS)UNSPECIFIED
Ishihara Sangyo Kaisha, Ltd.UNSPECIFIED
Heritage Medical Research InstituteUNSPECIFIED
American Cancer SocietyUNSPECIFIED
Issue or Number:11
Record Number:CaltechAUTHORS:20210202-123615131
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210202-123615131
Official Citation:Yasuaki Nakayama, Michael R. Maser, Tatsuya Okita, Anton V. Dubrovskiy, Taryn L. Campbell, and Sarah E. Reisman. Journal of the American Chemical Society 2021 143 (11), 4187-4192; DOI: 10.1021/jacs.1c01372
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:107875
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:02 Feb 2021 20:50
Last Modified:25 Jun 2021 19:22

Repository Staff Only: item control page