The Reduction of Prostaglandin Intermediates Using Alumino Hydride Reagents

Abstract

The assembly of the correct C-15¹ stereochemistry in prostaglandin synthesis has been attained by either generating the desired stereochemistry at C-15¹ through stereoselective reduction of a ketone precursor² or by adding the fully functionalised C₁₂-C₂₀ side chain intact by means of organometallic³, borane⁴ and β-oxidoylid reagents⁵. This paper is concerned with the first of these two approaches. It illustrates how a prostaglandin precursor (1) was reduced using bulky alumino hydride reagents derived from 3-0-benzyl-1,2,0-cyclohexylidene- α -D-glucofuranose to give benefits of yield or moderate stereoselectivity over other methods available at the time the work was carried out.