Regioselective lithiations of a pterocarpan skeleton: the first synthesis of (±)-4′-dehydroxycabenegrin A-I

Autor:	Alcides J. M. da Silva, Paulo R. R. Costa, Antonio L. Coelho, Alessandro B. C. Simas
Rok vydání:	2001
Předmět:	chemistry.chemical_compound chemistry Prenylation Stereochemistry Bromide Organic Chemistry Drug Discovery Electrophile Pterocarpan Regioselectivity Biochemistry Derivative (chemistry)
Zdroj:	Tetrahedron Letters. 42:4111-4113
ISSN:	0040-4039
Popis:	Maackiain O-MOM derivative 3b was regioselectively lithiated at the C-10 position of D-ring and reacted with electrophiles. Regioselective lithiation of the C-10 TMS-substituted derivative 5d, followed by organocopper formation and treatment with prenyl bromide, enabled the desired prenylation at C-4. The obtained compound 6d was employed in the first synthesis of racemic 4′-dehydroxycabenegrin A-I, 4. Moreover, dialkylation of 3b at the two most reactive sites could be effected through the generation of a dilithiated species. A preliminary result dealing with diethylcarbamate derivative 3c is also shown.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::813bf4c851bf6439ac50eac20c05a629 https://doi.org/10.1016/s0040-4039(01)00682-7 Zobrazit plný text záznamu Full Text from ScienceDirect