
%0 Journal Article
%A Bremner, John B. 
%A Keller, Paul A. 
%A Pyne, Stephen G. 
%A Robertson, Alan D. 
%A Skelton, Brian W. 
%A White, Allan H. 
%A Witchard, Helen M. 
%T The Synthesis of New Dibenzothiophen Amino Acid and Cyclophane Derivatives
%J Australian Journal of Chemistry
%D 2000/10/27
%V 53
%N 7
%P 535-540
%K Dibenzothiophen; amino acid derivatives; cyclophanes; Stille reaction; olefin metathesis.
%R https://doi.org/10.1071/CH00029
%U https://www.publish.csiro.au/paper/CH00029 
%X Some novel dibenzothiophen amino acid and cyclophane derivatives have been produced as a result of synthetic studies on the development of dibenzothiophen-based antibacterial compounds. Allylation through a Stille reaction has produced 2-allyl-8-bromodibenzothiophen (3a) and 2,8-diallyldibenzothiophen (3b). Under different conditions, the Stille reaction also produced 2-bromo-8-(prop-1-enyl)dibenzothiophen (4a) and 2,8-di(prop-1- enyl)dibenzothiophen (4b) via double bond isomerization. Olefin metathesis with (3b) and methyl N-acetylallylglycinate (5) produced two homodimers, the novel &#91;4&#93;(5,11)&#91;4&#93;(18,24)dibenzothiophenophane-2,15-diene (6), as a mixture of geometrical isomers, and dimethyl (E)- and (Z)-(R,S)-2,7-diacetamidooct-4-enedioate 8), and the two cross-metathesis products methyl (E)- and (Z)-(R,S)-2-acetamido-6-(8-allyldibenzothien-2-yl)hex-4-enoate (7a) and dimethyl (E)- and (Z)-(R,S)-6,6&cent;-(dibenzothiophen-2,8-diyl)bis(2-acetamidohex-4-enoate) (7b). Palladium-catalysed hydrogenation of the homodimer (6) and the cross-metathesis products (7a,b) yielded the corresponding reduced compounds (9) and (10a,b), respectively. 
