The two-step NaBH4/CeCl3 1,2-reduction of spiro[4,4]nonane-2,7-diene-1,6-di
one gave a trans- alcohol as a first product which reacted further to the c
orresponding cis,trans-diol. Pd(II)-catalysis was used to effect an allylic
rearrangement from the 1,6-diacetate to the corresponding 2,7-diacetate. B
oth diacetates were substrates for Pd(0)-catalyzed allylic alkylations. The
relative stereochemistry was retained. (C) 1999 Elsevier Science Ltd. All
rights reserved.