Abstract
Two procedures are described for the preparation of the racemic mevalonic lactone (±)-2, via a meso-dialdehyde 8. The preparation of compound 8 in seven steps from cyclopentadiene is also described. This procedure intends to be model for a desymmetrization study of dialdehyde 8, leading to optically active (-) (R)- and (+) (S)- mevalonolactone, 2.
Highlights
Mevalonic acid, which exists in an equilibrium between its open (–)-(R)-1 and cyclic form (mevalonolactone, (–)-(R)-2), is a key intermediate in cellular biochemistry.[1]. It is a precursor for a number of biologically important lipids, including cholesterol, steroid hormones, bile acids, ubiquinone and dolichols
Mevalonate-derived isoprenoids are intermediates in the biosynthesis of isoprenylated tRNAs, prenylated proteins involved in cell signaling and growth, and heme a, a prosthetic group of cytochrome oxidase
We present here a model study of the synthesis of racemic mevalonic acid lactone (±)-2, which can be applied to a enantioselective synthesis of (–)-(R)- and (+)-(S)- mevalonolactone, 2, as we have shown recently in the synthesis of (+)-(S)- and (–)-(R)- nor-methyl mevaldate derivatives.[16]
Summary
Mevalonic acid, which exists in an equilibrium between its open (–)-(R)-1 and cyclic form (mevalonolactone, (–)-(R)-2), is a key intermediate in cellular biochemistry.[1].
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