Toward the two-directional synthesis of the IJK-ring system of the marine polyether CTX3C

QD Chemistry

Gibbard, Helen ; Clark, J.S.

University:University of Glasgow

Department:School of Chemistry

关键词: marine polyether, two-directional, ring-closing metathesis, IJK-tricyclic core;   

Others  :  http://theses.gla.ac.uk/5889/1/2014gibbardphd.pdf

来源: University of Glasgow

【 摘 要 】

This thesis describes efforts made towards the two-directional synthesis of the IJK-tricyclic core of the H-M ring system of CTX3C.The first chapter serves as an introduction to the complex marine polyether natural products and details their toxicology and biosynthetic origins. A literature review of the advances made by our research group, as well as in other laboratories, towards the iterative and convergent synthesis of polycyclic ethers, with particular emphasis on the ciguatoxins is also included. This is followed by a review of olefin metathesis and the use of double ring-closing metathesis reactions for the preparation of complex polycyclic systems.The second chapter details the construction of two model systems to allow for investigation into the chemistry required for the synthesis of both the I- and K-rings. Following the successful construction of the two model systems, the chemistry developed was then employed in a two-directional strategy toward the synthesis of the target IJK-tricyclic core.