Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Optical Rotatory Dispersions of β-Hydroxylated 5β-Spirostanones
藤間 貞彦藤野 明治山崎 克彦木村 道也
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1972 年 20 巻 10 号 p. 2240-2245

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The β-axial hydroxylated 5β-spirostan-1- and 3-ones were prepared from the steroidal sapogenins in Convallaria and diosgenin, and the optical rotatory dispersion curves of these ketones were measured in methanol or dioxane. The 5-hydroxy-25 (R), 5β-spirostan-3-one (XIII) showed a weak positive amplitude (a : +16.0) in contrast to the negative one of the parent 3-ketone (I, a : -16.6). The hydroxyl groups substituted on the symmetrical β-axial positions to the carbonyl groups led to marked changes in the amplitude of Cotton effect in the 5β-spirostanones, and opposed to the prediction from the octant rule.
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© The Pharmaceutical Society of Japan
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