Abstract
Part 1: The Human Immunodeficiency Virus (HIV) was first found by scientists at the Institute Pasteur in Paris. Among the two types of HIV, HIV-1 is the one that has been broadly spread around the world. According to the World Health Organization (WHO), 30 million people are living with HIV/Acquired Immune Deficiency Syndrome (AIDS) worldwide, and 690,000 people died of HIV-related illnesses worldwide in 2019. Although the development of antiretroviral therapies has improved the quality of patients’ lives, the cost of treatment, the global distribution, and the fast mutation of the virus make vaccine development urgent. In the first and second chapters, the synthesis of Man9-(GlcNac)2-N3 (1.10) and Mann-(Cyclohexyl)-N3, key compounds in HIV vaccine design, will be discussed.
Part 2: Allylation has been widely used to prepare homoallylic alcohols and amines, which could be used as building blocks for the synthesis of complex natural products. Among allylic reagents, allyl boranes and allyl boronates have been widely utilized to react with aldehydes under the activation of Lewis acid. Inspired by these reactions, our group developed homoallylboration between cyclopropylcarbinyl boronates and vialdehydes. Our homoallylboration shows great stereoselectivity and high yield. In the third
chapter, the synthesis of γ-substituted cyclopropylcarbinyl boronates, along with the effect of the substituents on the cyclopropyl ring on homoallylation, will be discussed.