Sequential Enyne-Metathesis/Diels-Alder Strategy: Rapid Access to Sugar-Oxasteroid-Quinone Hybrids

A sequential enyne-metathesis/Diels-Alder strategy is reported for the synthesis of a new class of sugar-oxasteroid-quinone hybrid molecules. 1,2:5,6-Di-O-isopropylidine-d-glucose was chosen as a chiral-pool starting material. Various sugar-derived enynes were synthesised from the common starting material. Dienes derived from these enynes were treated with various quinone dienophiles under Diels-Alder reaction conditions to give a library of sugar-oxasteroid-quinone hybrids