Metal-catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2-substituted-4-oxy- cyclopent-2-en-1-ones yielding prostaglandins and prostaglandin analogs

This invention provides a novel method for the preparation of 2,3- disubstituted-4-oxy-cyclopentan-l-one compounds that are useful for the synthesis of prostaglandins and prostaglandin analogs of industrial relevance. The method comprises the metal -catalyzed asymmetric 1,4-conjugate addition of vin...

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Bibliographic Details
Main Authors Wu, Hsyueh-Liang, Wen, Wen-Hsien, Henschke, Julian Paul, Wu, Ping-Yu
Format Patent
LanguageEnglish
Published 31.07.2020
Subjects
ACYCLIC OR CARBOCYCLIC COMPOUNDS
ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM
CHEMISTRY
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
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Summary:This invention provides a novel method for the preparation of 2,3- disubstituted-4-oxy-cyclopentan-l-one compounds that are useful for the synthesis of prostaglandins and prostaglandin analogs of industrial relevance. The method comprises the metal -catalyzed asymmetric 1,4-conjugate addition of vinylboron compounds to 2- substituted-4-oxy-cyclopent-2-en-l-ones. This method relies on the use of less toxic, easily- handled reagents, and can be performed under milder conditions than offered by some conventional methods, affording 2,3-disubstituted-4-oxy-cyclopentan-l-one compounds enantio- and diastereoselectively, which are precursors to the said prostaglandin and prostaglandin analogs, in high yield.
Bibliography:Application Number: NZ20150727773