Studies on the Syntheses of Heterocyclic Compounds. CDLXXXVII. Photolytic Synthesis and Rearrangement of Proerythrinadienones

TETSUJI KAMETANI; KEIICHI TAKAHASHI; TOSHIO HONDA; MASATAKA IHARA; KEIICHIRO FUKUMOTO

doi:10.1248/cpb.20.1793

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363

Studies on the Syntheses of Heterocyclic Compounds. CDLXXXVII. Photolytic Synthesis and Rearrangement of Proerythrinadienones

TETSUJI KAMETANI, KEIICHI TAKAHASHI, TOSHIO HONDA, MASATAKA IHARA, KEIICHIRO FUKUMOTO

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1972 Volume 20 Issue 8 Pages 1793-1799

DOI https://doi.org/10.1248/cpb.20.1793

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Abstract

Photolysis of the 1-(2-bromobenzyl)-1, 2, 3, 4-tetrahydro-7-hydroxyisoquinolines (VII, VIII, and X) gave the proerythrinadienones (XIII, XIV, and XV), which would be key precursors for several isoquinoline alkaloids. The acidic treatment of these dienones and the corresponding dienols (XXXII) was investigated under several conditions.

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