Wieland–Miescher ketone

• 9 -methyl-5 (10) - octalin -1 ,6- dione
• 8a -methyl-3, 4,8,8 a- tetrahydro- -1.6 (2H, 7H)- naphthalindion

Beige solid

Fixed

47-50 ° C

109-115 ° C (at 6.7 Pa )

Template: Infobox chemical / molecular formula search available

The Wieland - Miescher ketone is an organic chemical compound. Is a bicyclic diketone which is saturated except for one double bond.

The Wieland - Miescher ketone is named after its discoverers Peter Wieland and Karl Miescher, who developed it at Ciba- Geigy. The actual Wieland - Miescher ketone is obtained in racemic form by a Robinson annulation, of pharmaceutical interest, however, the enantiomerically pure representation.

Representation

The Wieland - Miescher ketone was first prepared by a Robinson annulation. The second step of the Robinson annulation ( aldol reaction) was carried out here on organokatalytischem way over the Eder -Sauer- Wiechert- Hajos- Parrish reaction. Served as organocatalyst enantiomerically pure (S )-proline which could be obtained with high enantioselectivity the product.

The synthesis can be carried out as a one-pot reaction. The aldol intermediate was isolated only from Hajos and Parrish and described in their patent.

Use

The Wieland - Miescher ketone is of synthetic interest for the pharmaceutical industry. It serves as the starting compound for the total synthesis of steroids.