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.