BUTENOLIDE ANNELATIONS USING A MANGANESE(III) OXIDATION - A SYNTHESIS OF JOLKINOLIDE-E

Date

1995-01-01

Author

DEMIR, AS
Tanyeli, Cihangir
AKGUN, H
CALISKAN, Z
OZGUL, E

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A general procedure was developed for the annelation of a butenolide to an enone that highlighted a manganese(III) oxidation of an enone. The merit of this procedure was illustrated in a synthesis of (-)-jolkinolide E, ent-1, from (+)-manool 11. A potassium permanganate-mediated degradation of 11 and dehydration of an intermediate beta-hydroxyketone 12 according to a literature procedure afforded a tricyclic enone 13. Oxidation of 13 with manganese(III) acetate and chloropropionic acid regio- and stereoselectively furnished a C-12 alpha chloropropionyl ester 14. An Arbuzov reaction of 14 with triethylphosphite and an intramolecular Horner-Emmons cyclization of the resulting phosphonate 15 gave (-)-jolkinolide E, the structure of which was investigated in detail by NMR. This methodology was also applied to 4,4-dimethylcyclohex-2-en-1-one. This overall approach offers a general solution to the problem of butenolide annelation to enones.

Subject Keywords

(-)-Jolkınolıde e, Manganese(ııı) acetate oxıdatıon, Butenolıde annelatıon

URI

https://hdl.handle.net/11511/55029

Journal

BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE

Collections

Department of Chemistry, Article

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Citation Formats

A. DEMIR, C. Tanyeli, H. AKGUN, Z. CALISKAN, and E. OZGUL, “BUTENOLIDE ANNELATIONS USING A MANGANESE(III) OXIDATION - A SYNTHESIS OF JOLKINOLIDE-E,” BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, pp. 423–427, 1995, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/55029.