Abstract
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.
Original language | English |
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Pages (from-to) | 3427-3429 |
Number of pages | 3 |
Journal | Organic Letters |
Volume | 5 |
Issue number | 19 |
Early online date | 28 Aug 2003 |
DOIs | |
Publication status | Published - 18 Sep 2003 |
Externally published | Yes |