Synthesis of antibacterial and biobased compounds
Chemical substances isolated from plants or microorganisms play a variety of roles in our society. They work as food sources, provide sustainable energy and cure diseases.
In the first chapter, four natural products and their derivatives exhibiting antibacterial activities were introduced and their total synthesis were described. Biatriosporin D, indanostatin, dihydro eurotiumide B and naphthacemycin A9 are bioactive hydroquinone/quinone natural products. The acylation and intramolecular Friedel Crafts reaction were the keys steps to the construction of the quinone structure in biatriosporin D. The Hauser-Kraus annulation was successfully applied to the syntheses of hydroquinone structures in indanostatin, dihydro eurotiumide B and naphthacemycin A9.
In the second chapter, two biobased pyrone compounds were utilized as the starting materials to synthesize a variety of chemical substances. Substituted isophthalates were synthesized from methyl coumalate and vinyl ethers. A variety of alkyl, aryl and heteroaryl isophthalates were prepared. Aldol reactions of dehydroacetic acid at the acetyl group with aldehydes have been achieved. A direct synthesis of pogopyrone A was accomplished in two steps.