Moran, Wesley J., Goodenough, Katharine M., Raubo, Piotr and Harrity, Joseph P. A. (2003) A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (−)-Deoxynupharidine. Organic Letters, 5 (19). pp. 3427-3429. ISSN 15237060

A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd−TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (−)-deoxynupharidine 1 is described.

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