Abstract:
Synthesis of anti-anti- and anti-syn-3,4:8,9-tetraacetoxy-11-oxa-tricyclo[4.4.1.0(1,6)] undecanes have been achieved starting from naphthalene. The Birch reduction of naphthalene gave 1,4,5,8-tetrahydro-naphthalene in high yield. 1,4,5,8-Tetrahydro-naphthalene was selectively oxidised with mCPBA to give 11-oxa-tricyclo[4.4.1.0(1,6)]undeca-3,8-diene. OsO4 oxidation followed by acetylation furnished the corresponding tetraacetates.