Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthesis of the Alkaloid, Xylopinine and the Related Compound by Photo-induced Rearrangement of Spiroisoquinoline
HIROSHI IRIEKIMIKO AKAGISHOHEI TANIKEIKO YABUSAKIHIROYUKI YAMANE
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1973 Volume 21 Issue 4 Pages 855-857

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Abstract
Photolysis of 1, 2, 3, 4-tetrahydro-6, 7, 4', 5'-tetramethoxyisoquinoline-1-spiro-2'-indan-1'-one (II) gave 5, 6-dihydro-2, 3, 10, 11-tetramethoxyberbinium salt (IV) which was further converted into 2, 3, 10, 11-tetramethoxyberbine (VI) by treatment with sodium borohydride. In the same reaction sequence, 1, 2, 3, 4-tetrahydro-6, 7, 5', 6'-tetramethoxyisoquinoline-1-spiro-2'-indan-1'-one (IX) was transformed into xylopinine (VII)
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© The Pharmaceutical Society of Japan
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