Abstract
The synthesis of (-)-cis-neocnidilide (1), a stereoisomer of neocnidilide (2) having inhibiting activity against mycotoxin-producing fungi, is described. (±)-(E)-1, 3-Nonadien-5-ol was kinctically resolved to give (S)-13, which was converted to (S)-triene ester 8. The intramolecular Diels-Alder reaction of 8 afforded a mixture of 12 and 10. The dihydro derivative 14, obtained by catalytic hydrogenation of 12, was transformed via trimethylsilylketene acetal into α-bromolactone 19, which upon treatment with DBU in toluene, gave rise to (-)-cis-neocnidilide (1).
