Abstract
The stereocontrolled synthesis of the extremely labile phthalic acid 4,5-cis-dihydrodiol(1) has been achieved in a highly efficient manner in seven steps from bis[2-(trimethylsilyl)ethyl] fumarate (2). The Diel-Alder adduct 3 of the fumarate with furan has been converted into first exo-cis-diol 4 and then its acetonide 5. Treatment of acetonide 5 with lithium hexamethyldisilazide result in the regioselective formation of olefinic alcohol 6. Following the introduction of the second double bond into the cyclohexene ring system
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