Complementary synthesis of organoboranes to populate the chemical functionality to a given area of biomedical interest

Identificador:  TDX:3047

Handle: https://hdl.handle.net/20.500.11797/TDX3047

Autors:  Royes Buisan, Jordi

Resum:
This thesis is related to the development of new synthetic methodologies to introduce boryl moieties in compounds with potential biomedical properties. Towards this end, boron sulfur reagents, geminal-diboryl reagents or the most common commercially available diboron reagent B2pin2, have been used in this thesis. The wide variety of boron containing reagents has allowed the development of new routes to provide cyclic products of high interest. The access to these building blocks can be achieved through two different main pathways: via deborylation or borylative cyclization. The first method is related to chapter 3, where the activation of polifunctional systems such as CH(B)(S)(Si) can be tuned by the addition of base giving access to alkylation reactions. Moreover, chapters 4 and 6 are related to the development of new methods for the borylative ring closing of alkenyl halides or aldehydes, to afford the formation of spiro bicyclic structures with a pendant boronate group and in the second case as well the incorporation of the hydroxyl unit with total control of the diastereoselectivity. The developed methodology described in chapter 4 was directly applied to chapter 5 for the synthesis of spiro bicyclic products which are susceptible to be drugs for the treatment of Alzheimer’s disease. That project was developed in collaboration with the pharmaceutical company Janssen Cilag, from Johnson & Johnson in Toledo.