Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Acid-catalyzed Rearrangement of Hinesol and Related Compounds to Eudesmane Derivatives
糸川 秀治中西 博三橋 進
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1983 年 31 巻 6 号 p. 1991-1997

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Acid-catalyzed rearrangement of hinesol α-epoxide (5a) gave 1α-hydroxyeudesmols (9, 10, 11) together with other spirane-type products (6, 8, 14). The same reaction of α-and β-epoxides of hinesol acetate also provided eudesmane derivatives. These results and mechanistic considerations led us to re-examine the formic acid dehydration reaction of hinesol and it was found that the main product does not have the structure 3 or 4 as assumed by Marshall et al., but is identical with (+)-δ-selinene (21).
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© The Pharmaceutical Society of Japan
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