Total synthesis of ( ±)-nitidanin and novel procedures for determination of the location of the side chains on 1,4-benzodioxane.

Kuboki, Atsuhito; Yamamoto, Toru; Taira, Mamie; Arishige, Tetsuya; Ohira, Susumu.

Regioselective cycloaddition of 5-[1,1-(ethylenedioxy)ethyl]-3-methoxy-1,2-benzoquinone and silyl-protected sinapyl alc. gave 1,4-benzodioxane (±)-I [R = SiMe2CMe3, R1 = 1-methyldioxolan-1-yl (II)], which was converted to the antimalarial (±)-nitidanin I (R = H, R1 = E-CH:CHCH2OH). Two novel procedures were developed to determine the location of the side chains of the adduct II based on partial ring cleavage. 

Tetrahedron Letters

Elsevier Ltd.

48

5

771

774