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Type: Journal article
Title: Syntheses of Angucyclinones Related to Ochromycinone. II. Regio-and Stereo-selective Reduction of a Tetrahydroangucyclinone
Author: Rozek, T.
Tiekink, E.
Taylor, D.
Bowie, J.
Citation: Australian Journal of Chemistry, 1998; 51(11):1057-1060
Issue Date: 1998
ISSN: 0004-9425
Abstract: <jats:p> The reduction of racemic 8-hydroxy-6-methoxy-3,3-dimethyl-3,4,5,6,6a,12a-hexahydrobenz[a]anthracene- 1,7,12(2H)-trione, with either (i) sodium borohydride and cerium(III) chloride in ethanol (the Luche reagent) or (ii) sodium borohydride in ethanol, was shown (by n.m.r. and X-ray crystallographic data) to yield the same racemic product, viz. 7,8-dihydroxy-6-methoxy-3,3-dimethyl-2,3,4,5,6,6a,7,12a-octahydrobenz[a]anthracene-1,12-dione. The 7-OH and 6-OMe groups are cis to each other. The observed regiochemistry can be rationalized in both cases by preferential interaction of respectively (i) the cerium(III) chloride of the Luche reagent, and (ii) sodium borohydride with the 8-OH group of (3) (the 8-OH group is more acidic than the solvent), while the cis stereochemistry is consistent with hydride delivery from the less hindered face in (3).</jats:p>
RMID: 0030002719
DOI: 10.1071/C98094
Appears in Collections:Chemistry publications

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