
%0 Journal Article
%A Cambie, RC 
%A Higgs, PI 
%A Rutledge, PS 
%A Woodgate, PD 
%T Annulations of Podocarpic Acid Derivatives via an Aryne Intermediate
%J Australian Journal of Chemistry
%D 1994/10/01
%V 47
%N 10
%P 1815-1831
%K 
%R https://doi.org/10.1071/CH9941815
%U https://www.publish.csiro.au/paper/CH9941815 
%X The cycloaddition of substituted furans to the diterpenoid aryne (39), generated by in situ diazotization of the anthranilic acid (1) followed by cleavage of the annulated 1,4- epoxydecahydrochrysenes, provides a convenient method for the preparation in high yield of the previously unknown 1-substituted octahydrochrysen-4-ols. Use of 1,3-dipoles under the same procedure, or under a modified procedure involving pre-isolation of the diazonium tetrafluoroborate salt (9), gave novel annulated heterocyclic products directly. Attempted [2+2] cycloadditions of electron-rich alkenes to the diterpenoid aryne (39) were largely unsuccessful but reaction with 1,1-dimethoxyethene by using in situ diazotization gave a product derived from an initial [2+2] cycloaddition. 
