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Macrocyclization of Di‐Boc‐guanidino‐alkylamines Related to Guazatine Components: Discovery and Synthesis of Innovative Macrocyclic Amidinoureas
Author(s) -
Castagnolo Daniele,
Raffi Francesco,
Giorgi Gianluca,
Botta Maurizio
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.200801109
Subject(s) - chemistry , stereochemistry , combinatorial chemistry
The synthesis of new and innovative macrocyclic amidinoureas from linear di‐Boc‐guanidino‐alkylamines related to guazatine was accomplished. The macrocyclization reaction proceeds under mild conditions affording 11‐ to 16‐membered rings with a new and previously undescribed structure in good yields. Enantiomerically pure macrocyclic amidinoureas were also synthesised. The strict correlation between macrocyclic amidinoureas and the natural productguazatine makes them very actractive also from a biological point of view. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)