Organic Letters 2012-06-01

Diastereocontrolled construction of pactamycin's complex ureido triol functional array.

Justin T Malinowski, Stefan J McCarver, Jeffrey S Johnson

Index: Org. Lett. 14(11) , 2878-81, (2012)

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Abstract

An advanced intermediate in a projected synthesis of pactamycin has been prepared. Early installation of the C1-dimethylurea functionality allows for its participation in a diastereoselective, chelation-controlled addition of organometal nucleophiles to the C5 prochiral ketone. Four of the molecule's six stereocenters are set with a ketone functional handle provided for subsequent manipulation.