Design And Synthesis Of Naphthoquinone Moiety For Rubromycins&The Synthesis Of Antitumor Drug NG25

This dissertation aims at the synthesis of highly substituted naphthoquinone which was required for the synthesis of the rubromycin family and the synthesis of NG25.It consists of the following three parts:Chapter 1 Review on the isolation,bioactivities,structural characterizations and the synthesis of naphthalene moieties.The first part related to the isolation,structural characterization,biological activities of the rubromycins.The concise synthesis of naphthalene compounds for incorporation into a synthetic sequence for the rubromycin family of natural products is reviewed.Chapter 2 Design and synthesis of naphthalene moietiesBased on the new spiroketalization methods developed by our group as key step,the new total synthesis strategys were proposed and several corresponding key intermediates were designed for the total synthesis of rubroycins.Through Diels-Alder reaction as key step,and from phenol derivatives as starting materials,these naphthalenes were synthesized.These are new approaches for the synthesis of naphthalene moieties for rubromycins,which has shorter scheme,higher yield and more easy operation.Using these intermediates,the total synthesis of rubromycins was explored,which is ongoing.Chapter 3 Synthesis and the modification of antitumor drug NG25The third part was mentioned the studies on the total synthesis of therapeutic antineoplastic agent NG25.We adopted a convergent synthesis strategy,using compound 88 as starting material,experiencing m-CPBA oxidation,nitrification,nucleophilic substitution,dechlorination and other steps.We developed a straightforward and more efficient method for synthesising NG25,sent masterstandard and technical supporting to the QA.