Issue 9, 2000

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

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.

Article information

Article type
Paper
Submitted
25 Nov 1999
Accepted
29 Feb 2000
First published
11 Apr 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 1439-1443

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

M. Lajunen and A. Koskinen, J. Chem. Soc., Perkin Trans. 1, 2000, 1439 DOI: 10.1039/A909471G

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