The top half models 11 and 25 of the antibiotic aglycone tetronolide (1) were prepared from tetrahydrophthalide and 2,4-hexadiene-l,6-diol in 8 and 12 steps, respectively. Compound 11 was coupled with the bottom half model 30a, which was prepared via Diels-Alder reaction of methacrolein with triene 27a or 33a to afford a-acyltetronate 38. The allyl chloride 39 derived from 38 was rather unstable, and attempts for macrocyclization resulted in decomposition of the key intermediate.
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