22 Migrated hopenesおよび関連トリテルペノイドの酸による転位反応と酸化成積体について
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概要
- 論文の詳細を見る
1. Acid induced migration of the migrated hopenes, i.e. filic-3-ene (Ia), adian-5-ene (IIa), fern-9(11)-ene (IIIa), fern-7-ene (IIIc), pteron-14-ene (IVa), neohop-12-ene (Va) gave various products including adian-5(10)-ene (IIb), fern-8-ene (IIIb), 8βH-fern-9(11)-ene (IIId), 9βH-fern-7-ene (IIIe), neohop-13(18)-ene (Vb) and hop-17(21)-ene (VIa) as shown as in Fig. 1. The results are remarkably different from those obtained in a case of migrated oleanenes, such as friedel-3-ene (I'a), glutin-5-ene (II'a), multiflor-7-ene(III'c), taraxer-14-ene (IV'a) and olean-12-ene (V'a). 2. Boiling of fern-9(11)-ene (IIIa) and 8βH-fern-9(11)-ene (IIId) with CrO_3 in acetic acid solutions afforded essentially fern-9(11)-en-12-one (VIII) and 18βH-fern-9(11)-en-12-one (IX), respectively. On the other hand, fern-8-ene (IIIb), fern-7-ene (IIIc) and ferna-7,9(11)-diene reacted with CrO_3 in acetic acid-benzene-CH_2Cl_2 solutions to give various products, such as fern-7-en-11-one (X), fern-9(11)-en-7-one (XI), fern-8-en-11-one (XII), fern-8-en-7-one (XIII), fern-8-en-7,11-dione (XIV), fern-7-en-6-one (XV) and pteron-14-ene-7-one as shown as in a chart. UV, IR, NMR and mass spectra of these compounds are discussed. 3. Correlation of fern-9(11)-ene (IIIa) and arbor-9(11)-ene (III"a) has been established. Fern-8-en-7-one (XIII) was oxidized to ferna-5,8-dien-7-one (XVIII), Zn/AcOH reduction of which gave 25-nor-ferna-5,7,9-trien-7-ol (XIX). 25-Nor-arbora-5,7,9-trien-7-ol (XIX") was also synthesized from arbora-7,9(11)-diene (VII") via arbor-9(11)-en-7-one (XI"), arbor-8-en-7-one (XIII") and arbora-5,8,11-trien-7-one (XVIII"). The fact that (XIX) and (XIX") are proved to be an optical antipode demonstrated that fernane and arborane skeletons have antipodal structures at the ring C, D and E.
- 天然有機化合物討論会の論文
- 1969-09-01
著者
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上田 博之
昭和薬大
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荒井 洋子
Showa College of Pharmaceutical Sciences
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塩島 憲治
昭和薬大
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荒井 洋子
昭和薬大
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Arai Y
Showa Pharmaceutical University
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塩島 憲治
昭和薬科大学
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