ARYNE CHEMISTRY OF PODOCARPIC ACID-DERIVATIVES

The anthranilic acid (2), a key intermediate for the generation of an aryne at C 13 of podocarpic acid derivatives, was synthesized from the 14-amino compound (5) which in turn was generated regiospecifically in high yield by treatment of the 13-bromo compound (25) with sodamide in liquid ammonia. T...

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Bibliographic Details
Published inAustralian journal of chemistry Vol. 47; no. 8; pp. 1483 - 1508
Main Authors CAMBIE, RC, HIGGS, PI, RUTLEDGE, PS, WOODGATE, PD
Format Journal Article
LanguageEnglish
Published COLLINGWOOD C S I R O PUBLICATIONS 01.01.1994
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
ORGANIC-SYNTHESIS
NUCLEOPHILIC CONDENSATIONS
COMPLEX BASES
NITRIC-ACID
TOTAROL
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Summary:The anthranilic acid (2), a key intermediate for the generation of an aryne at C 13 of podocarpic acid derivatives, was synthesized from the 14-amino compound (5) which in turn was generated regiospecifically in high yield by treatment of the 13-bromo compound (25) with sodamide in liquid ammonia. The amine was converted into the anthranilic acid by two separate routes: firstly by directed lithiation and trapping of the lithium species with a CO2 moiety, and secondly by oxidative cleavage of an isatin fused across positions 13 and 14.
ISSN:0004-9425
DOI:10.1071/CH9941483