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Concise Syntheses of Δ^(12)-Prostaglandin J Natural Products via Stereoretentive Metathesis

Li, Jiaming and Ahmed, Tonia S. and Xu, Chen and Stoltz, Brian M. and Grubbs, Robert H. (2019) Concise Syntheses of Δ^(12)-Prostaglandin J Natural Products via Stereoretentive Metathesis. Journal of the American Chemical Society, 141 (1). pp. 154-158. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20181212-100802379

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Abstract

Δ^(12)-Prostaglandin J family is recently discovered and has potent anticancer activity. Concise syntheses of four Δ^(12)-prostaglandin J natural products (7–8 steps in the longest linear sequences) are reported, enabled by convergent stereoretentive cross-metathesis. Exceptional control of alkene geometry was achieved through stereoretention.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/jacs.8b12816DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.8b12816PublisherSupporting Information
ORCID:
AuthorORCID
Li, Jiaming0000-0001-6646-5693
Xu, Chen0000-0002-3222-459X
Stoltz, Brian M.0000-0001-9837-1528
Grubbs, Robert H.0000-0002-0057-7817
Additional Information:© 2018 American Chemical Society. Received: November 29, 2018; Published: December 12, 2018. We acknowledge funding from NIH (R01GM031332 and R01GM080269) and NSF CHE 150216. T.S.A. acknowledges NSF for support through a graduate research fellowship. Materia, Inc. is thanked for generous donations of catalysts. A. W. Sun, E. R. Welin, and Y. Xu are thanked for helpful discussion and input on this paper. Dr. Scott C. Virgil (Caltech) is thanked for assistance with chiral-SFC and HPLC separation. K. Chen from F. H. Arnold lab is thanked for his help with Biotage separation. Dr. David VanderVelde (Caltech) and Dr. Mona Shahgholi (Caltech) are acknowledged for help in structural determination and characterizations. This paper is dedicated to Professor E. J. Corey on the occasion of his 90th birthday. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NIHR01GM031332
NIHR01GM080269
NSFCHE-150216
NSF Graduate Research FellowshipUNSPECIFIED
Issue or Number:1
Record Number:CaltechAUTHORS:20181212-100802379
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20181212-100802379
Official Citation:Concise Syntheses of Δ12-Prostaglandin J Natural Products via Stereoretentive Metathesis. Jiaming Li, Tonia S. Ahmed, Chen Xu, Brian M. Stoltz, and Robert H. Grubbs. Journal of the American Chemical Society 2019 141 (1), 154-158. DOI: 10.1021/jacs.8b12816
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:91707
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:12 Dec 2018 18:20
Last Modified:03 Oct 2019 20:37

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