A general access to 5,8-disubstituted indolizidine alkaloids has been developed, where the asymmetric addition of an optically active allenyltitanium to benzyl[4-(tert-butyldimethylsilyloxy)butylidene]amine (2) is the key reaction. As a typical example, (-)-indolizidine 209B was efficiently synthesi
✦ LIBER ✦
A new approach to indolizidine alkaloids: Asymmetric formal total synthesis of (−)-Swainsonine
✍ Scribed by Zhou Wei-Shan; Xie Wen-Ge; Lu Zhi-Hui; Pan Xin-Fu
- Publisher
- Elsevier Science
- Year
- 1995
- Tongue
- French
- Weight
- 219 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0040-4039
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Asymmetric intramolecular Heck cyclization of endocyclic enamides occurs at room temperature to give indoloizidine and azaazulene ring systems in up to 86% enantiomeric excess. A synthesis of (+)-epiindolizidine 167B and formal synthesis of 5E,9Z-indolizidine 223AB is described.