The development of one-pot multi-reaction processes for the synthesis of natural products and biologically active compounds

QD Chemistry

Calder, Ewen D. D. ; Andrew, Sutherland

University:University of Glasgow

Department:School of Chemistry

关键词: Chemistry, Organic chemistry, Synthesis, Natural product, Overman rearrangement, One-pot multi-reaction processes;   

Others  :  http://theses.gla.ac.uk/6667/1/2015calderphd.pdf

来源: University of Glasgow

【 摘 要 】

This thesis is divided into four chapters in which one-pot processes have been developed and utilised for the synthesis of biologically active compounds. The work in the first chapter outlines the 13-step total synthesis ofD -ribo- andL - arabino-phytosphingosine fromD -ribose. This process employed a microwave promoted Overman rearrangement of an allylic trichloroacetimidate to install the amine functionality.In the second and third chapters, the development of a one-pot, two-step Overman/ring closing metathesis process is detailed. The synthesis of three different classes of starting material is also shown. This one-pot process was used as the key step in the synthesis of four oxybenzo[c]phenanthridine natural products and the partial synthesis of an ACAT inhibitor. The potential for further functionalisation of the products by oxidation and reduction was also explored.In the final chapter, a one-pot allylboration/Heck process for the synthesis of indan-1-ols is described. Optimisation and an investigation of the scope of the process are also presented. The process was then altered to allow the use of a chiral phosphoric acid catalyst for the asymmetric synthesis of these compounds.