Open AccessStudies on the syntheses of heterocyclic compounds. Part 782. Another total synthesis of (±)-tubulosine and (±)-deoxytubulosine
Author(s) -
Tetsuji Kametani,
Yukio Suzuki,
Masataka Ihara
Publication year - 1979
Publication title -
canadian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.323
H-Index - 68
eISSN - 1480-3291
pISSN - 0008-4042
DOI - 10.1139/v79-269
Subject(s) - chemistry , tryptamine , aluminum hydride , pyridine , sodium hydride , pictet–spengler reaction , total synthesis , sodium , hydride , organic chemistry , catalysis , hydrogen , biochemistry , methoxide
(±)-Tubulosine (1) and (±)-deoxytubulosine (3) were totally synthesized by the Pictet–Spengler reaction of (±)-4-oxoprotoemetine (7) with serotonin (8) or tryptamine (9) followed by reduction with sodium bis(2-methoxyethoxy)aluminum hydride in pyridine.
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