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Synthesis of Azabenzisochromanquinone Antibiotics, I. Hetero Diels‐Alder Reactions of Isochromanquinones with 1‐Aza‐1,3‐dienes
Author(s) -
Tödter Carsten,
Lackner Helmut
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960908
Subject(s) - chemistry , regioselectivity , cycloaddition , ring (chemistry) , quinone , diene , stereochemistry , antibiotics , combinatorial chemistry , total synthesis , medicinal chemistry , organic chemistry , catalysis , natural rubber , biochemistry
The total synthesis of a novel type of benzisochromanquinone antibiotics 2 containing nitrogen in the aromatic ring A is described. Three different isochromanquinone building blocks ( 6, 10 , and 14 ) were subjected to cycloaddition reactions with five diverse 1‐aza‐1,3‐butadienes 15–17, 19 yielding three groups of structurally modified 6‐ and 9‐aza compounds: azaeleutherins 21–24 , azaepinanaomycins 26–31 , and 1‐methylazakalafungins 32–39 . The regioselectivity of the reaction depends on the substituents at the diene and the structural symmetry of the quinone. The strategy provides a convenient access to a broad palette of structural variants. Particularly some azakalafungins show remarkable antibacterial and antitumor activities.