Hajos-Parrish ketone: approaches toward C-ring prcursors of 7-deoxytaxol

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Abstract

Two routes were evaluated for the preparation of multiply functionalized cyclohexane derivatives in a stereocontrolled fashion from readily available Hajos–Parrish ketone 1. Reduction (catalytic or dissolving metal) led to the cis-isomer 8, in stark contrast to previous literature. Finally, modification of earlier steroid chemistry allowed the synthesis of the trans-isomer 14. The latter is a useful intermediate for the synthesis of 7-deoxytaxol derivatives.

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Original languageEnglish
Pages (from-to)1439-1443
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number1
Publication statusPublished - 2000
MoE publication typeA1 Journal article-refereed

    Research areas

  • synthesis, taxol

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