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Enantioselective Synthesis of 15-Deoxy-Δ¹²,¹⁴-Prostaglandin J₂

Li, Jiaming and Stoltz, Brian M. and Grubbs, Robert H. (2019) Enantioselective Synthesis of 15-Deoxy-Δ¹²,¹⁴-Prostaglandin J₂. Organic Letters, 21 (24). pp. 10139-10142. ISSN 1523-7060. https://resolver.caltech.edu/CaltechAUTHORS:20191209-080257479

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1021/acs.orglett.9b04198DOIArticle
ORCID:
AuthorORCID
Li, Jiaming0000-0001-6646-5693
Stoltz, Brian M.0000-0001-9837-1528
Grubbs, Robert H.0000-0002-0057-7817
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.
Funders:
Funding AgencyGrant Number
NIHR01GM031332
NIHR01GM080269
Issue or Number:24
Record Number:CaltechAUTHORS:20191209-080257479
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20191209-080257479
Official Citation:Enantioselective Synthesis of 15-Deoxy-Δ12,14-Prostaglandin J2. Jiaming Li, Brian M. Stoltz, and Robert H. Grubbs. Organic Letters 2019 21 (24), 10139-10142. DOI: 10.1021/acs.orglett.9b04198
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:100228
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:09 Dec 2019 18:20
Last Modified:07 Jan 2020 22:37

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