Question

Natural products that contain the N-1,1-dimethyl-2-propenyl group (called an N-reverse prenyl group) often exhibit antitumor or antifungal activity. The synthesis of a particular N-reverse prenylated indole antifungal compound begins with the two steps shown below (Tetrahedron Lett. 2001, 42, 7277–7280):

Challenge Problem 09.77 Natural products that contain the N-1,1-dimethyl-2-propenyl group (called an N-reverse prenyl group) often exhibit antitumor or antifungal activity. The synthesis of a particular N-reverse prenylated indole antifungal compound begins with the two steps shown below (Tetrahedron Lett. 2001, 42, 7277-7280): COAC → C13H5N Cuci, l-Pr,NET

Answer 1

Mechanism i - PrNet Cuci H O AC SN² type attack Het Cigtig Regah 1 equiv. H2 - Pd-catalyst

1 09.77 al н I I I I -= - H compound - F13 Hign