Stereoselective total synthesis of Aspergillide D.

The total synthesis of the 16-membered Polyhydroxylated macrolide, Aspergillide D has been accomplished utilizing the Grignard reaction, Sharpless asymmetric epoxidation Regioselective ring opening of epoxy alcohol, Wittig olefination and Yamaguchi macrolactonisation as key steps. 3-butene-1-ol has been utilized as the starting material.

Me3Al-mediated domino nucleophilic addition/intramolecular cyclisation of 2-(2-oxo-2-phenylethyl)benzonitriles with amines; a convenient approach for the synthesis of substituted 1-aminoisoquinolines.

A simple and efficient protocol for the construction of 1-aminoisoquinolines was achieved by treating 2-(2-oxo-2-phenylethyl)benzonitriles with amines in the presence of Me3Al. The reaction proceeds via a domino nucleophilic addition with subsequent intramolecular cyclisation. This method provides a wide variety of substituted 1-aminoisoquinolines with good functional group tolerance. Furthermore, the synthetic utility of this protocol was demonstrated in the successful synthesis of the antitumor agent CWJ-a-5 in gram scale.