Published July 6, 2018
| Accepted Version + Supplemental Material
Journal Article
Open
An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol
- Creators
-
Xu, Chen
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Han, Arthur
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Reisman, Sarah E.
Abstract
An approach to synthesize the pentacyclic framework of the polyol diterpenoid ryanodol is reported. The ABC tricycle was constructed by a Co-mediated Pauson–Khand reaction, and both radical and anionic cyclization pathways were developed to form the E-ring. In addition, a reaction sequence involving SeO_2-mediated enone oxidation and hydroxyl-directed oxy-Michael addition was developed to introduce the A-ring oxidation. The feasibility of forming the bridging D-ring by an oxidative dearomatization was established.
Additional Information
© 2018 American Chemical Society. Received: May 2, 2018; Published: June 13, 2018. Accession Codes: CCDC 1840855 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K.; fax: +44 1223 336033. We thank Dr. Michael Takase and Larry Henling (both of Caltech) for X-ray data collection and Ms. Julie Hofstra (Caltech) for X-ray data refinement. Dr. Scott Virgil and the Caltech Center for Catalysis and Chemical Synthesis are gratefully acknowledged for access to analytical equipment. Fellowship support was provided by the Shenzhen UV-ChemTech Inc. (C.X.), and the NIH (A.H., Nos. 5T32GM007616-37 and 1F31GM120821). S.E.R. is a Heritage Medical Research Institute Investigator. Financial support from the NIH (Nos. NIGMS RGM097582-01 and R35GM118191-01), Eli Lilly, and Novartis is gratefully acknowledged. The authors declare no competing financial interest.Attached Files
Accepted Version - nihms-984975.pdf
Supplemental Material - ol8b01387_si_001.pdf
Files
nihms-984975.pdf
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Additional details
- PMCID
- PMC6103443
- Eprint ID
- 87056
- DOI
- 10.1021/acs.orglett.8b01387
- Resolver ID
- CaltechAUTHORS:20180613-100330914
- Shenzhen UV-ChemTech Inc.
- 5T32GM007616-37
- NIH Predoctoral Fellowship
- 1F31GM120821
- NIH
- Heritage Medical Research Institute
- RGM097582-01
- NIH
- R35GM118191-01
- NIH
- Eli Lilly
- Novartis
- Created
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2018-06-13Created from EPrint's datestamp field
- Updated
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2022-03-10Created from EPrint's last_modified field
- Caltech groups
- Heritage Medical Research Institute