Abstract
Abstract: Solanoeclepin A shows significant hatch-stimulating activity for the potato cyst nematodes. In this thesis, we focused on the synthesis of tricyclo[5.2.1.01,6]decane skeleton of solanoeclepin A, including four-, five- and six-membered ring bearing three consecutive quaternary stereocenters. We have achieved the quarternalization of C-1 carbon via [2,3]-Wittig rearrangement and the construction of tricyclo[5.2.2.01,6]undecene system 5 through titanocene-mediated radical cyclization from epoxide 4. The synthesis started from Hajos-Parrish ketone 1 and it was converted to E-unsaturated ester 2 in a few steps including Horner-Wadsworth-Emmons (HWE) reaction. After multi-steps synthesis, the precursor 3 was subjected to [2,3]-Wittig rearrangement conditions to yield 4 and its isomer. Next, titanocene-mediated radical cyclization afforded the tricyclo[5.2.2.01,6]undecene framework.