CaltechAUTHORS
Published January 9, 2019 | Version Supplemental Material
Journal Article Open

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

Creators

  • 1. ROR icon California Institute of Technology
  • 2. ROR icon Southern University of Science and Technology

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.

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.

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Supplemental Material - ja8b12816_si_001.pdf

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ja8b12816_si_001.pdf

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Additional details

Identifiers

Eprint ID
91707
Resolver ID
CaltechAUTHORS:20181212-100802379

Funding

NIH
R01GM031332
NIH
R01GM080269
NSF
CHE-150216
NSF Graduate Research Fellowship

Dates

Created
2018-12-12
Created from EPrint's datestamp field
Updated
2021-11-16
Created from EPrint's last_modified field