
TY  - JOUR
A1  - Cambie, RC 
A1  - Higgs, PI 
A1  - Rutledge, PS 
A1  - Woodgate, PD 
T1  - Annulations of Podocarpic Acid Derivatives via an Aryne Intermediate
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1994
VL  - 47
IS  - 10
SP  - 1815
EP  - 1831
KW  - 
UR  - https://doi.org/10.1071/CH9941815 
N2  - 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. 
ER  -

