合成路线1

Treatment of 2-methyl-3-butyn-2-ol (I) with trifluoroacetic anhydride and DBU gave trifluoroacetate (II), which was condensed with 4-bromophenol (III) in the presence of CuCl2 to afford propargyl ether (IV). Cyclization of (IV) in N,N-diethylaniline at 185 C produced benzopyran (V). The required sulfonyl group was introduced in (V) by lithium-bromine exchange, followed by reaction with sulfur dioxide to give the lithium sulfinate (VI), and then oxidation to the sulfonyl chloride (VII) by means of sulfuryl chloride (1). Subsequent treatment of (VII) with diisobutylamine yielded sulfonamide (VIII). Asymmetric epoxidation of (VIII) using sodium hypochlorite and (S,S)(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino-manganese(III) chloride (Jacobsen's catalyst) gave rise to epoxide (IX), which was opened with ammonium hydroxide to furnish the trans aminoalcohol (X). Finally, coupling of (X) with N-chlorophenyl-N'-cyanothiourea (XI) in the presence of EDC provided the title cyanoguanidine derivative.