Abstract
Solanoeclepin A 1 shows significant hatch-stimulating activity for the potato cyst nematodes. In this thesis, we focused on the synthesis of the tetracyclic diene 152,including 7-oxabicyclo[2.2.1]heptane moiety, six- and seven-membered ring bearing six chiral centers.The 7-oxabicyclo[2.2.1]heptane moiety was obtained via a diastereoselective IMDA (intramolecular Diels-Alder reaction) strategy by using a chiral auxiliary (S)-(-)-4-methoxy-α-methylbenzylamine as the source for this synthesis.This synthesis started from 106 and it was converted to enyne 140 in seven steps. After complexation of acetylene 140 with Co2(CO)8, the cyclization precursor 144 was obtained and subjected to intramolecular Prins-Carbonyl-Ene cyclization via Me2AlCl catalysis to yield stereoselective cyclic product 148a. Next, removal of cobalt afforded the tetracyclic diene 152 framework.