
%0 Journal Article
%A Mander, LN 
%A Potter, GJ 
%A Pyne, SG 
%A Woolias, M 
%T Studies on gibberellin synthesis. The preparation of phenanthrenoid intermediates for the synthesis of gibberellin A<sub>21</sub>
%J Australian Journal of Chemistry
%D 1981/09/01
%V 34
%N 9
%P 1913-1919
%K 
%R https://doi.org/10.1071/CH9811913
%U https://www.publish.csiro.au/paper/CH9811913 
%X Methyl 3-(6'-oxo-4'-methoxy-5',6',7',8'-tetrahydronaphthalen-1'-yl)propanoate (11) was converted by conventional methods into diazoketone (17) which underwent acid-promoted cyclization to dienone (18). Refunctionalization gave dienone (20) which was subjected to a tandem alkylation, conjugate addition process with the sodium enolate of dimethyl malonate to furnish a 2: 1 mixture of dimethyl (2RS,8aSR,10aSR)-2-methoxymethyloxy-10,12-dioxo-2,3,4,5,6,7,8a,9,10-decahydro-1 H-2,10a-ethano- phenanthrene-8,8-dicarboxylate (21) and its 8a-epimer, respectively. Subsequent manipulations led to lactone (26), but attempts to convert this compound into a gibbane derivative were unsuccessful. 
