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

Jiaming Li; Brian M Stoltz; Robert H Grubbs

doi:10.1021/acs.orglett.9b04198

Enantioselective Synthesis of 15-Deoxy-Δ^12,14-Prostaglandin J₂

Org Lett. 2019 Dec 20;21(24):10139-10142. doi: 10.1021/acs.orglett.9b04198. Epub 2019 Dec 6.

Authors

Jiaming Li¹, Brian M Stoltz², Robert H Grubbs¹

Affiliations

¹ The Arnold and Mabel Beckman Laboratory of Chemical Synthesis, Division of Chemistry and Chemical Engineering , California Institute of Technology , Pasadena , California 91125 , United States.
² The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering , California Institute of Technology , 1200 East California Boulevard, MC 101-20 , Pasadena , California 91125 , United States.

PMID: 31808699
DOI: 10.1021/acs.orglett.9b04198

Abstract

An enantioselective synthesis of 15-deoxy-Δ^12,14-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-Δ^12,14-prostaglandin J₂ in high enantiopurity.

Publication types

Research Support, N.I.H., Extramural

MeSH terms

Molecular Structure
Prostaglandin D2 / analogs & derivatives*
Prostaglandin D2 / chemical synthesis
Prostaglandin D2 / chemistry
Stereoisomerism

Substances

9-deoxy-delta-9-prostaglandin D2
Prostaglandin D2

Abstract

Publication types

MeSH terms

Substances

Grants and funding