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Título

The reversible Nicholas reaction in the synthesis of highly symmetric natural-product-based macrocycles

Autor Torre, María C. de la ; Asenjo, María ; Ramírez-López, Pedro; Sierra, Miguel A.
Palabras clave Steroids
Cobalt
Dynamic covalent chemistry
Macrocycles
Fecha de publicación 2015
EditorJohn Wiley & Sons
Citación European Journal of Organic Chemistry 2015: 1054-1067 (2015)
ResumenTwo different approaches to highly symmetric macrocycles by reversible Nicholas reactions have been developed. The first sequence uses a bis[Co2(CO)6] complex derived from a double propargylic alcohol supporting two natural product moieties. The reactions with BF3·OEt2 and different benzene dimethanols yielded either (1:1) or (2:2) adducts, depending essentially on the nature of the tether joining both Co clusters. Alternatively, the Nicholas reactions of Co-complexed propargyl alcohol templates with one steroid and one monoterpene fragment as well as one aromatic terminus containing an alcohol moiety yielded the corresponding macrocycles derived from self-dimerization. Both routes to macrocycles are complementary and efficiently produce sophisticated natural-product-containing structures.
URI http://hdl.handle.net/10261/111951
DOI10.1002/ejoc.201403541
Identificadoresdoi: 10.1002/ejoc.201403541
issn: 1434-193X
e-issn: 1099-0690
Aparece en las colecciones: (IQOG) Artículos
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