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Synthesis of 9‐Substituted‐1,8‐Dioxooctahydroxanthenes by an Efficient Iodine‐Catalyzed Cyclization
Author(s) -
Luna Liliana E.,
Cravero Raquel M.,
Faccio Ricardo,
Pardo Helena,
Mombrú Álvaro W.,
Seoane Gustavo
Publication year - 2009
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/ejoc.200801233
Subject(s) - chemistry , iodine , adduct , michael reaction , catalysis , molecule , tandem , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
New 1,8‐dioxooctahydroxanthenes with substituents in the 2‐, 3‐, and 9‐positions were obtained by cyclization with iodine from tandem Michael/Michael adducts. The X‐ray molecular structure of the methyl 2‐(1,8‐dioxo‐2,3,4,5,6,7,8,9‐octahydro‐1 H ‐xanthen‐9‐yl)acetate ( 3a ) was solved and shows the parallel laminae packing of these molecules. Furthermore, we reported the structure of intermediate 4 isolated from this reaction. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)