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Synthesis 1999; 1999(3): 415-422
DOI: 10.1055/s-1999-3402
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Studies Toward the Synthesis of Menogaril: Synthesis of A-Ring Precursors and Their Conversion to the Tetracyclic Core via the Benzannulation Reaction

William D. Wulff* , Jing Su, Peng-Cho Tang, Yao-Chang Xu
  • *Department of Chemistry, Searle Chemistry Laboratory, The University of Chicago, Chicago, IL 60637, USA; Fax +(7 73)7 08 08 05; E-mail: wulff@rainbow.uchicago.edu
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Publication Date:
31 December 1999 (online)

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A model study for the synthesis of menogaril is reported which involves the benzannulation reaction of a Fischer carbene complex with an alkyne that contains the A-ring of the tetracyclic core of menogaril. The synthesis of methoxy and benzyloxy derivatives of this alkyne are reported as well as the reaction of the methoxy derivative with an o-methoxyphenyl carbene complex to generate a tricyclic naphthol containing three of the four rings of menogaril core. Completion of the model study and the synthesis of the tetracyclic anthracyclinone core of menogaril was accomplished by an intramolecular Friedel-Crafts cyclization.

benzannulation reaction - Fischer carbene complex - Friedel-Crafts cyclization - anthracyclinones - menogaril