Use of malic acid as a chiral synthon: 24,25-Dihydroxycholecalciferol

✍ Scribed by Jeffrey Sterling; Eliot Slovin; Dinorah Barasch

• Book ID: 104227154
• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 222 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95394-2

✦ Synopsis

A new chiral synthon prepared from malic acid is introduced and utilized in a synthesis of 24,25_dihydroxycholecalciferol.

Despite the increasing sophistication and stereoselectivity of synthetic methods of generating 1 new chiral centers , the high optical purity of naturally occurring chiral molecules often makes this the method of choice for the introduction of asymmetry. Malic acid has often been used as a chiral synthon 2. , ~n part because of its availability in both enantiomeric forms 3 .

Its use has been limited, however, by the difficulty in differentiating chemically between its two carboxylate groups.