Hladezuk, I;Chastagner, V;Collins, SG;Plunkett, SJ;Ford, A;Debarge, S;Maguire, AR

2012

February

Tetrahedron

Development of O-H insertion for the attachment of phosphonates to nucleosides; synthesis of alpha-carboxy phosphononucleosides

Validated

Altmetric: 4 ()

ANTI-HIV ACTIVITY CARBENOID MEDIATED CYCLIZATIONS INTRAMOLECULAR BUCHNER REACTION CYCLIC ETHERS REVERSE-TRANSCRIPTASE DIAZO-COMPOUNDS PHOSPHONOMETHOXY NUCLEOSIDES PROTECTING GROUPS N-DEBENZOYLATION DNA-POLYMERASES

68

1894

1909

Development of rhodium catalysed O-H insertion reactions employing alpha-diazophosphonates with appropriately protected adenosine, uridine and thymidine derivatives is described. This synthetic methodology leads, following deprotection, to novel phosphononucleoside derivatives bearing a carboxylic acid moiety adjacent to the phosphonate. Protection strategies are critical to the success of the key O-H insertion. There are two important aspects: avoiding competing insertion pathways or catalyst poisoning, and being able to achieve deprotection without degradation of the phosphononucleosides. (C) 2012 Elsevier Ltd. All rights reserved.

OXFORD

0040-4020

10.1016/j.tet.2011.12.077