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New Amino Endoperoxides Belonging to the Antimalarial G‐Factor Series
Author(s) -
Givelet Cécile,
Bernat Virginie,
Danel Mathieu,
AndréBarrès Christiane,
Vial Henri
Publication year - 2007
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.200700086
Subject(s) - chemistry , diastereomer , amine gas treating , aldehyde , stereochemistry , reactivity (psychology) , amino acid , hexacoordinate , organic chemistry , biochemistry , silicon , medicine , alternative medicine , pathology , catalysis
In the search for new antimalarial endoperoxides we developed a direct route for the preparation of new amino compounds belonging to the G‐factor series. During the synthesis, a significant difference in reactivity between two series of diastereoisomers was observed. The final amino endoperoxides were obtained with 58 to 70 % yields, depending on the starting amine, in the “ anti” series, but with the “ syn” diastereoisomers an unexpected rearrangement occurred during the deprotection step. This was attributed to a transient hexacoordinate fluorosilicon complex allowing the formation of a 1,2‐dioxetane. Its decomposition gave aldehyde 12 and 4‐hydroxybutan‐2‐one; these compounds were also identified when acidic conditions were used in the deprotection step. The anti amino compounds obtained were tested, but in vitro activities were found to be lower than initially expected, and fitted poorly with the previous biological hypothesis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)