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Synthesis of Phenanthro[9,10‐ b ]indolizidin‐9‐ones, Phenanthro[9,10‐ b ]quinolizidin‐9‐one, and Related Benzolactams by Pd(OAc) 2 ‐Catalyzed Direct Aromatic Carbonylation
Author(s) -
Yamashita Satoshi,
Kurono Nobuhito,
Senboku Hisanori,
Tokuda Masao,
Orito Kazuhiko
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801047
Subject(s) - chemistry , catalysis , quinolizidine , ring (chemistry) , electrophilic aromatic substitution , carbonylation , medicinal chemistry , palladium , stereochemistry , organic chemistry , alkaloid , carbon monoxide
Phenanthro[9,10‐ b ]indolizidin‐9‐ones, phenanthro[9,10‐ b ]quinolizidin‐9‐one, and related benzolactams were synthesized by benzolactam ring formation using Pd(OAc) 2 ‐catalyzed direct aromatic carbonylation. This also constitutes a formal synthesis of the representative phenanthroindolizidine and ‐quinolizidine alkaloids (±)‐tylophorine, (±)‐antofine, and (±)‐cryptopleurine.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)