Synthesis of enantiopure cis-decalins from microbially-derived cis-1,2-dihydrocatechols

Abstract

The microbially-derived cis-1,2-dihydrocatechol 3 is converted, via reaction sequences involving Diels–Alder cycloaddition and anionic oxy-Cope rearrangement steps, into the enantiopure cis-decalins 15 and 26; using simple modification of this chemistry the pseudo-enantiomer 22 of decalin 15 is also prepared from diol 3.