CaltechAUTHORS
  A Caltech Library Service

An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol

Xu, Chen and Han, Arthur and Reisman, Sarah E. (2018) An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol. Organic Letters, 20 (13). pp. 3793-3796. ISSN 1523-7060. PMCID PMC6103443. https://resolver.caltech.edu/CaltechAUTHORS:20180613-100330914

[img] PDF - Accepted Version
See Usage Policy.

1MB
[img] PDF (Experimental procedures, characterization data (1H and 13C NMR, HRMS, FTIR) for all new compounds) - Supplemental Material
See Usage Policy.

5MB

Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20180613-100330914

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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.8b01387DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/acs.orglett.8b01387PublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6103443PubMed CentralArticle
ORCID:
AuthorORCID
Xu, Chen0000-0002-3222-459X
Han, Arthur0000-0001-8691-699X
Reisman, Sarah E.0000-0001-8244-9300
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.
Group:Heritage Medical Research Institute
Funders:
Funding AgencyGrant Number
Shenzhen UV-ChemTech Inc.UNSPECIFIED
NIH Predoctoral Fellowship5T32GM007616-37
NIH1F31GM120821
Heritage Medical Research InstituteUNSPECIFIED
NIHRGM097582-01
NIHR35GM118191-01
Eli LillyUNSPECIFIED
NovartisUNSPECIFIED
Issue or Number:13
PubMed Central ID:PMC6103443
Record Number:CaltechAUTHORS:20180613-100330914
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180613-100330914
Official Citation:An Oxidative Dearomatization Approach To Prepare the Pentacyclic Core of Ryanodol. Chen Xu, Arthur Han, and Sarah E. Reisman. Organic Letters 2018 20 (13), 3793-3796. DOI: 10.1021/acs.orglett.8b01387
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:87056
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:13 Jun 2018 18:01
Last Modified:03 Oct 2019 19:51

Repository Staff Only: item control page