A Practical Synthesis of Enantiopure (R)-4-Hydroxy-2-cyclohexen-1-one

✍ Scribed by Gebauer, Olaf ;Brückner, Reinhard

• Publisher: John Wiley and Sons
• Year: 1996
• Tongue: English
• Weight: 590 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619961010

✦ Synopsis

Abstract

The title compound R‐4a was prepared from (–)‐quinic acid (1) in 6 steps in 18% overall yield (Scheme 3) and with 100% enantiomeric purity (Figure 1). The initiating step is the regio‐ and stereoselective acetalization of the trans‐oriented vicinal OH groups of 1 (+ 5 → 8). Alcohol R‐4a can be protected as the 2‐ethoxyethyl ether R‐4e (78%).