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
![]() |
PDF
- Accepted Version
See Usage Policy. 419kB |
![]() |
PDF (Characterization data, and experimental data)
- Supplemental Material
See Usage Policy. 7MB |
Use this Persistent URL to link to this item: https://resolver.caltech.edu/CaltechAUTHORS:20181212-100802379
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: |
| ||||||||||
ORCID: |
| ||||||||||
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: |
| ||||||||||
Issue or Number: | 1 | ||||||||||
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 | ||||||||||
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: | 16 Nov 2021 03:43 |
Repository Staff Only: item control page