An efficient stereocontrolled synthesis of functionalized chlorodienes and chlorotrienes
✍ Scribed by Margarita Mladenova; Mouâd Alami; Gérard Linstrumelle
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 175 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
Stereoselective reduction of conjugated homopropargylic alcohols 1 followed by an elimination reaction, allows an efficient approach to stereodefined (E,E,E)-chlorotrienes. The interest of these chlorotrienes was illustrated by a stereocontrolled synthesis of navenone B and all E conjugated polyenes
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Typical example: (3-Formylpropyl)benzoate 2c (19.2 g, 0.1 mol) was mixed with methyl acrylate 3 (13 g; 14 mL; 0.15 mol). After addition of DABCO (1.6 g, 0.015 mol) the resulting homogeneous mixture was allowed to stand at room temperature until 2c was no longer detectable (cu. 7 days). The remaining