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Total Synthesis of the Indolizidinium Alkaloid Ficuseptine
Author(s) -
Bracher Franz,
Daab Jochen
Publication year - 2002
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 - 10.1002/1099-0690(200207)2002:14<2288::aid-ejoc2288>3.0.co;2-g
Subject(s) - chemistry , sonogashira coupling , alkaloid , total synthesis , palladium , derivative (finance) , halogenation , alkynylation , organic chemistry , suzuki reaction , chloride , catalysis , stereochemistry , financial economics , economics
The first total synthesis of ficuseptine [4,6‐bis(4‐methoxyphenyl)‐1,2,3‐trihydroindolizidinium chloride] ( 1 ), an alkaloid from Ficus septica , is described. The crucial steps in this five‐step synthesis are a palladium‐catalyzed bis(arylation) of a dibromopyridine under Suzuki conditions and a palladium‐catalyzed alkynylation of an iodopyridine under Sonogashira conditions, as well as a novel Sandmeyer‐type iodination of a 2‐aminopyridine derivative. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)