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J Am Chem Soc. 2010 Feb 17;132(6):1802-3.

Annulation of thioimidates and vinyl carbodiimides to prepare 2-aminopyrimidines, competent nucleophiles for intramolecular alkyne hydroamination. Synthesis of (-)-crambidine.

Perl NR, Ide ND, Prajapati S, Perfect HH, Durón SG, Gin DY.

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Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, New York 10065, USA.

Abstract

A convergent synthesis of (-)-crambidine is reported. The sequence capitalizes on two novel key transformations, including a [4+2] annulation of thioimidates with vinyl carbodiimides and an alkyne hydroamination employing 2-aminopyrimidine nucleophiles.

PMID:: 20095555; [PubMed - indexed for MEDLINE]
PMCID:: PMC2839241

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