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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Approaches to a Key Lactone Intermediate Required for the Synthesis of Pyranonaphthoquinone Antibiotics

MA Brimble and JA Spicer

Australian Journal of Chemistry 44(2) 197 - 205
Published: 1991

Abstract

Addition of 2-trimethylsilyloxyfuran (19) to naphthoquinone (20) gave in 91% yield the furo [3,2-b] naphtho [2,1-d]furan (18) which upon treatment with ceric ammonium nitrate gave the hydroxy ester (24) in 70% yield. Attempts to induce an intramolecular transesterification of hydroxy ester (24) to bislactone (6), a key intermediate required for the synthesis of several pyranonaphthoquinone antibiotics, were unsuccessful. Hydroxy ester (24), however, is closely related to the antibiotic juglomycin (32).

https://doi.org/10.1071/CH9910197

© CSIRO 1991

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