Aqueous metal-mediated reactions and their applications in organic syntheses
Description
The research includes two parts: methodology studies of aqueous metal-mediated reactions and total syntheses Part one. Methodology studies. Section 1: Aqueous indium-mediated allylation of various aldehydes with 3-bromo-2-chloro-1-propene was studied. This was followed by examination of ozonolysis of the product to yield beta-hydroxyl esters Section 2: A study of aqueous manganese-copper mediated allylation reaction between aryl aldehydes and allyl chloride showed exclusive chemoselectivity between arylaldehydes and aliphatic aldehydes Section 3: Aqueous rhodium-catalyzed phenylation reaction of trialkylphenylstannane with aldehydes and aqueous rhodium-catalyzed conjugated 1,4-addition reaction of trialkylphenylstannane and trialkylvinylstannane with alpha,beta-unsaturated esters and ketones under an air atmosphere were studied Part two. Total syntheses. Section 1: (+)-goniofufurone was synthesized from D-glucurono-6,3-lactone through an aqueous indium-mediated regio- and diastereoselective allenylation of carbonyl compounds as a critical step Section 2: 1,2-dideoxy-l-phenyl-beta-D-ribofuranose was synthesized from D-mannatol through an aqueous indium-mediated diastereoselective allylation of carbonyl compounds and Suzuki coupling reaction as critical steps Section 3: Several oligomers based on chiral 1,1'-binaphthol with 3,3'-acetylene spacer was synthesized and characterized through the palladium-catalyzed coupling reaction of aryliodides with acetylene