Quercus lactone synthesis

Such a sequence has been successfully used115 for the synthesis of 4-methyl-3-heptanol, the major constituent of the aggregation pheromone of the elm bark beetle (Scolytus multistriatus Marsham)117 and zir-butyM-methyltetrahydro-2-furanone118 known as quercus lactone or oak lactone. ... 

The regio- and diastereo-selective reaction of the anion generated from 2-(l-propen-l-yl)-l,3-dithiane with an aldehyde is applicable to the synthesis of rraru-p,y-disubstituted y-lactones, inciting the natural products ( )-eldnolide and ( )-rram-quercus lactone. ... 

When employing enantioenriched l-titano-2-alkenyl carbamates 334 in carbonyl addition, the selectivity depends on the enantiomeric purity that was achieved in its preparation (see Section IV.C.l). The (ii)-crotyl derivative (R)-334a has been employed several times (equation 92)224,252,253 optically active homoaldol products 346 are easily converted into y-lactones 347 by four different pathways, which require an oxidation step (see Section IV.C.6). Appfications in target synthesis include the natural products (-b)-quercus... 

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