Abstract
A concise synthetic route has been developed for the preparation of the naturally occurring isocoumarin cytogenin and NM-3, an analogue with anti-angiogenic activity. The route is general and also provided C(3) side chain modified analogues. Key aspects of the synthesis include orthogonal protection of the two aromatic alkoxy groups, benzylic lithiation and carboxylation, use of the resulting carboxylic acid in a DCC-promoted acylation of Meldrums acid, and facile ester enolate alkylations for introduction of side chains for convenient generation of a new set of NM-3 analogues.
Keywords: anti-angiogenic, cytogenin, benzylic lithiation, ester enolate alkylation, isocoumarins, NM-3
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...read more
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