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Acyl radical insertion for the direct formation of new 7-substituted pterin analogs.

ABSTRACT: A variety of pterin molecules were synthesized via an under-utilized acyl radical insertion, using aldehydes and alpha-keto esters as the acyl source. These reactions gave complete regiospecificity for the 7-isomer, with reaction times ranging in minutes, often with instantaneous product precipitation. This approach led to the construction of new pterin analogs unaccessable via traditional Friedel-Crafts acylation. The compounds were characterized by NMR spectroscopy and high-resolution mass spectroscopy.

SUBMITTER: Pruet JM

PROVIDER: S-EPMC2860152 | biostudies-other | 2010 May

REPOSITORIES: biostudies-other

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Acyl radical insertion for the direct formation of new 7-substituted pterin analogs.

Pruet Jeff M JM Robertus Jon D JD Anslyn Eric V EV

Tetrahedron letters 20100501 18

A variety of pterin molecules were synthesized via an under-utilized acyl radical insertion, using aldehydes and alpha-keto esters as the acyl source. These reactions gave complete regiospecificity for the 7-isomer, with reaction times ranging in minutes, often with instantaneous product precipitation. This approach led to the construction of new pterin analogs unaccessable via traditional Friedel-Crafts acylation. The compounds were characterized by NMR spectroscopy and high-resolution mass spe ...[more]

PMID: 20436939

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