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Diastereoselektive Synthese von Anthracyclinon‐Vorläufern
Author(s) -
Flock Markus,
Nieger Martin,
Breitmaier Eberhard
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199319930175
Subject(s) - chemistry , stereoselectivity , cycloaddition , stereochemistry , stacking , medicinal chemistry , organic chemistry , catalysis
Diastereoselective Synthesis of Anthracyclinone Precursors [4 + 2] Cycloaddition of various dienes such as 1‐acetoxy‐1,3‐butadienes 4a , b or 1‐phenylethyloxy‐1,3‐butadienes 4c – g with 1,4‐anthraquinones 3 affords tetracyclic precursors of anthracyclinone. Using the chiral substituted 1,3‐butadienes 4 cycloadducts with d.e. > 98% are obtained. The high stereoselectivity is explained by π stacking.