Abstract
The complete pentacyclic core of the melodinus alkaloid scandine has been synthesized. The synthetic strategy features two key steps: (1) a tandem nitroalkene conjugate addition/[3+2] cycloaddition of the resulting silyl nitronate and (2) an intramolecular Heck reaction of an aryl iodide with a γ-disubstituted allylic alcohol which set a highly congested, quaternary stereogenic center with the concomitant formation of an aldehyde. Intramolecular reductive amination with this aldehyde completed the pentacyclic core.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 2397-2402 |
| Number of pages | 6 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 348 |
| Issue number | 16-17 |
| DOIs | |
| State | Published - Nov 2006 |
Keywords
- Conjugate addition
- Nitroalkenes
- Quaternary stereogenic centers
- Silyl nitronates
- [3+2] cycloaddition
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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