27 22-Isoecdysoneの合成および22-Hydroxycholesterolの22-水酸基のconfigurationについて
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概要
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Klyne and Stokes reported that the hydroxyl group at C-22 in natural 22-hydroxycholesterol (26) is α_F-oriented. In connection with studies on the synthesis of ecdysone in our laboratory, it was found that this assignment should be reversed. Lactone A (3) and B (4) were prepared from stigmasterol (1) by eight steps of reactions as key, intermediates for the synthesis of ecdysone and its isomer at C-22 (41). These lactones were introduced into diol A (5) and B (6), respectively, which were also synthesized from stigmasterol by another route. 5α-Cholestane-3β,22-diol (15a), in which the configuration at C-22 is apparently different from that of natural 22-hydroxycholesterol, was obtained by transformations from diol A (5). (Chart 2) The similar treatment of diol B (6) afforded 5α-cholestane-3β,22-diol (25b) identical with the hydrogenation product of natural 22-hydroxycholesterol. (Chart 3) On the other hand, 22-isoecdysone (41) was synthesized from lactone A (3) (Chart 4), and ecdysone from lactone B (4). Thus, the configuration of the 22-hydroxyl group in natural 22-hydroxycholesterol is the same as that of ecdysone. If the configuration assigned in ecdysone is considered to be unequivocal, natural 22-hydroxycholesterol must be formulated as 5-cholestene-3β,22β_F-diol.
- 1968-09-20
著者
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沢井 政信
Research Laboratory Teikoku Hormone Mfg. Co. Ltd.
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森 弘
Chemical Research Department Teikoku Hormone Mfg. Co. Ltd.
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常田 清
Research Laboratory, Teikoku Hormone Mfg. Co., Ltd.
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森 弘
帝国臓器化研部
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柴田 健雄
帝国臓器化研部
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常田 清
帝国臓器化研部
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沢井 政信
帝国臓器化研部
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柴田 健雄
Research Department Teikoku Hormone Mfg. Co. Ltd.
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常田 清
Research Laboratory Teikoku Hormone Mfg. Co. Ltd.
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