An asymmetric synthesis of (-)-geosmin 1 via highly diastereoselective reduction of the enantiomerically pure title ketone 3 is described. Diisobutylaluminum hydride reduction of 3 in a mixed solvent of tetrahydrofuran and 1,2-dimethoxyethane led to aUylic alcohol 4 in 96% d.e., which by recrystalli
A highly efficient synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine via a double Suzuki reaction and a Chichibabin cyclization
โ Scribed by Michael Palucki; David L Hughes; Nobuyoshi Yasuda; Chunhua Yang; Paul J Reider
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 64 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
Synthesis of 2-[3-aminopropyl]-5,6,7,8-tetrahydronaphthyridine was accomplished via a one-pot double Suzuki reaction followed by deprotection and a highly regioselective intramolecular Chichibabin cyclization. A variety of reactions conditions were screened for the Chichibabin cyclization including choice of base, solvent and reaction temperature.
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