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 15237060Metadata only available from this repository.
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.
|Subjects:||Q Science > Q Science (General)|
Q Science > QD Chemistry
|Schools:||School of Applied Sciences|
School of Applied Sciences > Biomolecular Sciences Research Centre
|Depositing User:||Graham Stone|
|Date Deposited:||24 Apr 2009 11:39|
|Last Modified:||02 Jun 2009 13:40|
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