The common indolizidine core leading to the allopumiliotoxins was synthesized using an intramolecular (Z)-N-4-alkenylnitrone cycloaddition reaction as the key step. The synthesis began with (R)-tert-butyl-3-hydroxypent-4-enoate which was obtained via enzymatic resolution using Amano PS lipase.
Towards Allopumiliotoxins: A Concise Synthesis of the Indolizidine Core
โ Scribed by Bodduri V. D. Vijaykumar; Pitchakuntla Mallesham; Srivari Chandrasekhar
- Publisher
- John Wiley and Sons
- Year
- 2011
- Tongue
- English
- Weight
- 553 KB
- Volume
- 2012
- Category
- Article
- ISSN
- 1434-193X
No coin nor oath required. For personal study only.
๐ SIMILAR VOLUMES
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
We describe a concise and convergent route to the core matrix of the cortistatin steroidal alkaloids. The salient features of the synthesis are the Snieckus cascade methodology and the Masamune alkylative dearomatization. This chemistry lends itself to a total synthesis of the cortistatins and to th