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Abstract: 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.