As a part of our work in the development of novel antimalarials, we were interested in elaborating an appropriate synthetic strategy for the preparation of endoperoxide-containing bridged bicyclic scaffolds. Through a TMSOTf-promoted dehydrative cyclization strategy we synthesized 2,3,8-trioxabicyclo[3,3,1] nonane endoperoxides. Alkyl substituents at C4 of the bicyclic scaffold could be readily introduced through exposure to Grignard reagents. © 2013 Elsevier Ltd. All rights reserved.
Gemma, S., Kunjir, S., Brindisi, M., Novellino, E., Campiani, G., Butini, S. (2013). A synthetic strategy to bridged 2,3,8-trioxabicyclo[3,3,1]nonane endoperoxides. TETRAHEDRON LETTERS, 54(10), 1233-1235 [10.1016/j.tetlet.2012.12.075].
A synthetic strategy to bridged 2,3,8-trioxabicyclo[3,3,1]nonane endoperoxides
Gemma, Sandra;Kunjir, Sanil;Campiani, Giuseppe;Butini, Stefania
2013-01-01
Abstract
As a part of our work in the development of novel antimalarials, we were interested in elaborating an appropriate synthetic strategy for the preparation of endoperoxide-containing bridged bicyclic scaffolds. Through a TMSOTf-promoted dehydrative cyclization strategy we synthesized 2,3,8-trioxabicyclo[3,3,1] nonane endoperoxides. Alkyl substituents at C4 of the bicyclic scaffold could be readily introduced through exposure to Grignard reagents. © 2013 Elsevier Ltd. All rights reserved.
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https://hdl.handle.net/11365/43993
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