Gold-catalyzed nucleophilic substitution on propargylic alcohols, with various C-, O-, and S-nucleophiles, is described under very mild conditions (room temperature, dichloromethane) in 0-97% yield.

The Lewis acid-mediated direct amination of benzylic alcohols is described, providing various benzylic amine derivatives in good yields under mild and environmentally benign conditions. Among the different Lewis acids tested, goldA C H T U N G T R E N N U N G (III) proved to be the catalyst of choice for both chemical (yield, conversion) and practical reasons (a filtration over a silica pad is generally sufficient to obtain the corresponding benzylic amine in analytically pure form).

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The preparation of the C4-C24 fragment of the macrolactin A is described. The adopted synthetic strategy involves two isomerizations to selectively construct the (8E,10Z) and (16E,18E) dienes, using a sequential Claisen rearrangement/allene isomerization and a Ph3P-catalyzed isomerization of an yne-one, respectively.