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A Practical Synthesis of Enantiopure (R)-4-Hydroxy-2-cyclohexen-1-one (1996)

Gebauer, Olaf ; Brückner, Reinhard

Weinheim : Wiley-Blackwell

Liebigs Annalen 1996 (1996), S. 1559-1563

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ISSN: 0947-3440

Keywords: Chiral building blocks ; Quinic acid ; Regioselective acetalization ; Regioselective protection ; Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: 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%).

Additional Material: 1 Ill.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/jlac.199619961010

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