A synthetic approach to fusicoccin A utilizing intramolecular photocycloadd
ition of tethered 2-pyridones has been completed. This study has led to the
first solvent-dependent 2-pyridone photocycloaddition yielding either cis
or trans products. Epoxidation of the cis photoproduct is selective for the
disubstituted alkene, stabilizes the product, and is properly located for
installation of the trans-1,2-diol. Activation of the secondary amide by re
action with an isocyanate led to the reduction of the neopentyl amide carbo
nyl to a methyl group. (C) 1999 Elsevier Science Ltd. All rights reserved.