Published December 20, 2019
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Journal Article
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Enantioselective Synthesis of 15-Deoxy-Δ¹²,¹⁴-Prostaglandin J₂
Abstract
An enantioselective synthesis of 15-deoxy-Δ¹²,¹⁴-prostaglandin J₂ is reported. The synthesis begins with the preparation of enantiopure 3-oxodicyclopentadiene by a lipase-mediated kinetic resolution. A three-component coupling followed by a retro-Diels–Alder reaction provides the C8 stereochemistry of the prostaglandin skeleton with high enantioselectivity. Stereoretentive olefin metathesis followed by a Pinnick oxidation affords 15-deoxy-Δ¹²,¹⁴-prostaglandin J₂ in high enantiopurity.
Additional Information
© 2019 American Chemical Society. Received: November 22, 2019; Published: December 6, 2019. The authors acknowledge the funding from NIH (R01GM031332 and R01GM080269). Materia, Inc. is thanked for generous donations of catalysts. Dr. Scott C. Virgil (Caltech) is thanked for assistance with chiral-SFC and HPLC separation. Dr. Zepeng Yang (Caltech) is thanked for assistance with HPLC data collection. Dr. William Wolf, Carina Jette, and Zach Sercel (Caltech) are thanked for helpful discussion and input on this manuscript. Dr. David VanderVelde (Caltech) and Dr. Mona Shahgholi (Caltech) are acknowledged for assistance with characterization. The authors declare no competing financial interest.Attached Files
Supplemental Material - ol9b04198_si_001.pdf
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ol9b04198_si_001.pdf
Additional details
Identifiers
- Eprint ID
- 100228
- DOI
- 10.1021/acs.orglett.9b04198
- Resolver ID
- CaltechAUTHORS:20191209-080257479
Related works
- Describes
- 10.1021/acs.orglett.9b04198 (DOI)
Funding
- NIH
- R01GM031332
- NIH
- R01GM080269
Dates
- Created
-
2019-12-09Created from EPrint's datestamp field
- Updated
-
2021-11-16Created from EPrint's last_modified field