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Synthesis 1991; 1991(1): 33-36
DOI: 10.1055/s-1991-26373
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The Use of 1,4-Dipolar Aryne Cycloaddition Strategy in Anthracyclinone Synthesis: The Formal Synthesis of (±)-4-Demethoxydaunomycinone

Subhash P. Khanapure* , Edward R. Biehl
  • *Department of Chemistry, Southern Methodist University, Dallas, TX 75275, USA
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Publication Date:
17 September 2002 (online)

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We report herein the convergent synthesis of the 7,8,9,10-tetrahydro-9-hydroxy-6,11-dimethoxy-5,12-naphthacenedione (9), an advanced intermediate in the synthesis of (±)-4-demethoxy-daunomycinone, using the aryne dipolar cycloaddition reaction of lithiated 3-cyanophthalide and 2-bromo-5,6-dihydro-1,4-dimethoxynapththalene (6) in the key step. Similarly, the non-convergent synthesis of the 7,8-dihydro-4,6,11-trimethoxy-5,12-naphthacenedione (10), an important intermediate in the synthesis of (±)-daunomycinone, is presented.

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