Studies On Synthesis Of Fragment Of Ineleganolide

Allylic oxidation is especially useful and important because it provides corresponding allylic alcohols or α,β-unsaturated carbonyl compounds, which are the key intermediates in natural products synthesis. Hence, lots of reagents and conditions for allylic oxidation to be used in total synthesis of natural product have been reported. This thesis study the synthesis of the fragment of Marine natural products Ineleganolide, focusing on the selective oxidation of double bonds of S-Perillaldehyde.This thesis is composed of four chapters.The first chapter is composed of two parts. In the first part, the selenium and chromium reagents as allylic oxidants in natural products syntheses were reviewed. In the other part, the transition metal reagents as allylic oxidants in natural products synthesis were reviewed.In chapter2, two approaches towards the synthesis of the skeleton A of Ineleganolide were discussed. The first route, starting from S-Perillaldehyde features an epoxidation to furnish the Ineleganolide fragment analogue synthesis. The second route, has studied the double bond of selective allyl oxidation of S-Perillaldehyde.In chapter3, an efficient method for the asymmetric synthesis of the Ineleganolide fragment has been further developed. In this new route, starting from S-a-Pinene, the key steps of the synthesis are epoxidation and a Lewis acid mediated formation of the key intermediate. Finally the synthesis of block A in five steps with25%overall yield was finished.In the last chapter, the experiment procedure, spectrum data for all compounds described in Chapter2and Chapter3were recorded.