Synthesis of 1-Hydroxybicyclo[3.2.1]oct-3-en-2-ones by Acyloin Rearrangement of 1-Methoxy- or 1-tert-Butyldimethylsilyloxy-bicyclo[2.2.2]oct-5-en-2-ones

Abstract

1-Hydroxy- or 1, 8-dihydroxy-bicyclo[3.2.1]oct-3-en-2-ones were obtained from 1-methoxy- or 1-tert-butyldimethylsilyloxy-bicyclo[2.2.2]oct-5-en-2-ones via successive processes involving demethylation or desilylation and acyloin rearrangement by reaction with acids or tetra-n-butylammonium fluoride (TBAF).