Stereoselective Synthesis of Enantiomerically Pure Nupharamine Alkaloids from Castoreum

2009/02/07 by Alexander Stoye, Gabriele Quandt, Björn Brunnhöfer +5 · 1 citation
Chemistry · Biochemistry, Genetics and Molecular Biology · #Chemical synthesis and alkaloids #Marine Sponges and Natural Products #Synthesis and Biological Activity

paper · pdf · doi:10.1002/anie.200805606

openalex publication_date 2009/02/07 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

Abstract

An animalic note: The first total synthesis of the all-cis nupharamine 2, an alkaloid from beaver castoreum, is based on the stereoselective domino Mannich-Michael reaction of N-galactosylfurylaldimine to give 1 (Piv = pivaloyl), subsequent conjugate cuprate addition, and stereoselective protonation of the enolate. These reactions are all controlled by the carbohydrate. Protonation of the enolate after cleavage of the auxiliary leads to epimer 3.

Citations

• Zur Kenntnis der stickstoffhaltigen Inhaltsstoffe von Castoreum

Cited by

• Castoreum [wikipedia]

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