An Enantioselective Route to trans-2,6-Disubstituted Piperidines. -It is shown that trans-2,6-disubstituted piperidines can be prepared enantioselectively via (3 + 2) nitrone cycloaddition. This method is applied to the synthesis of the fire ant venom alkaloid (+)-solenopsin-A (IX). -
An enantioselective route to trans-2,6-disubstituted piperidines
β Scribed by Samuel Chackalamannil; Yuguang Wang
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 390 KB
- Volume
- 53
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
The synthesis of (S)-2-methyl tetrahydropyridine-N-oxide (4), a key intermediate for the enantioselective construction of trans-2,6-disubsdtuted piperidines via [3+2] nitrone cycloaddition reaction, is described. Nitrone 4 was elaborated to the fire ant venom alkaloid (+)-solenopsin-A (2) via intermediate 14.
π SIMILAR VOLUMES
An efficient six-step stereospecific synthesis of trans-2,Gdiphenylquinuclidine (1) is described together with an effective resolution of 1 into pure enantiomers. A key step in the synthesis is a highly efficient, catalyzed Diels-Alder reaction. Although the quinuclidine ring is an important struct
A new diastereoselective synthesis of 2,6-disubstituted piperidinic alkaloids is presented. Three natural compounds, the (-)-pinidinone 1a, the (+)-dihydropinidine 1b and the (-)-pinidinol 1c were prepared from optically pure (6R)-6-methylpiperidin-2one 2. This method is based on the chemo-and diast