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Synthesis of Ellipticine by Hetaryne Cycloadditions − Control of Regioselectivity
Author(s) -
Díaz Maite,
Cobas Agustín,
Guitián Enrique,
Castedo Luis
Publication year - 2001
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(200112)2001:23<4543::aid-ejoc4543>3.0.co;2-#
Subject(s) - regioselectivity , chemistry , stereochemistry , cycloaddition , combinatorial chemistry , computational chemistry , organic chemistry , catalysis
We have modified Gribble’s and Moody’s approaches to ellipticines by introducing substituents into the 3,4‐didehydropyridine dienophile to control the key cycloaddition step. A chloro substituent at position 2 improved the yields and the regioselectivities of the cycloadditions and the overall efficiency of the synthesis of ellipticine.