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Highly Efficient, Enantioselective Total Synthesis of the Active Anti‐Influenza A Virus Indole Alkaloid Hirsutine and Related Compounds by Domino Reactions
Author(s) -
Tietze Lutz F.,
Zhou Yifa
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990712)38:13/14<2045::aid-anie2045>3.0.co;2-u
Subject(s) - cycloaddition , indole test , enantioselective synthesis , domino , chemistry , knoevenagel condensation , alkaloid , stereochemistry , organic chemistry , catalysis
A very short reaction sequence consisting of a domino Knoevenagel/hetero‐Diels–Alder reaction with subsequent solvolysis and hydrogenation, provides the indole alkaloid hirsutine, which greatly inhibits the growth of influenza A viruses, and related compounds in enantiomerically pure form (see reaction scheme). The facial differentiation of the cycloaddition can be reversed by simple variation of the substituents on the indole nitrogen atom (H/ t BuOCO). Cbz=benzyloxycarbonyl.