Tetrahedron

Terpene und terpenderivate—IX: α-Curcumen, β-curcumen und ar-turmeron durch alkylierung von C5-und C10-dithianen

HH Bokel, A Hoppmann, P Weyerstahl

Index: Bokel, H. H.; Hoppmann, A.; Weyerstahl, P. Tetrahedron, 1980 , vol. 36, # 5 p. 651 - 654

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Citation Number: 9

Abstract

The dithiane 11 is alkylated with prenyl bromide to give 12. Hydrogenolysis of 12 with Raney- Nickel yields α-curcumene (6), hydrolysis of 12 gives the ketone 13. Prenal dithiane (14) is alkylated with 8 to give 15. ar-Turmerone (16) is formed by hydrolysis of 15. Reaction of 15 with sodium in liquid ammonia leads to a mixture of α-curcumene (6) and β-curcumene (10).