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. doi:10.1021/jacs.8b12816. 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:

URL	URL Type	Description
https://doi.org/10.1021/jacs.8b12816	DOI	Article
https://pubs.acs.org/doi/suppl/10.1021/jacs.8b12816	Publisher	Supporting Information

ORCID:

Author	ORCID
Li, Jiaming	0000-0001-6646-5693
Xu, Chen	0000-0002-3222-459X
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 Agency	Grant Number
NIH	R01GM031332
NIH	R01GM080269
NSF	CHE-150216
NSF Graduate Research Fellowship	UNSPECIFIED

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DOI:

10.1021/jacs.8b12816

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

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ID Code:

91707

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

12 Dec 2018 18:20

Last Modified:

16 Nov 2021 03:43

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