Asymmetric synthesis of solenopsins A, B and C
✍ Scribed by Guy Solladié; Nathalie Huser
- Book ID
- 104589725
- Publisher
- Elsevier Science
- Year
- 2010
- Tongue
- English
- Weight
- 467 KB
- Volume
- 114
- Category
- Article
- ISSN
- 0165-0513
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✦ Synopsis
Abstract
Solenopsins A, B and C have been synthesized in enantiomerically pure forms from the corresponding anti‐1,5‐diols which have been obtained from glutaric anhydride by an asymmetric synthesis induced by chiral sulfoxides.
📜 SIMILAR VOLUMES
## Abstract magnified image Concise and efficient methods for the synthesis of enantiomers of fire ant venom alkaloids solenopsin and isosolenopsin A, B, and C are described. These syntheses are based on diastereoselective electrophilic substitution of enatiomerically‐pure α‐lithiated 2‐alkylpiper
The trans-pip&dine alkaloid, (-)-solenopsin A. was prepared in seven steps from readily available 4-~haxy-3\_(niiropropyrsilyllpyrfdin in 43% overall yield. The addition of organ~tallics to chiral 1-acylpyridinium salt 1 gives N-acyl-2-alkyl-23&hydta~4pyridones 2 with high diastereoselectivity.\*~ T
Effective and convenient syntheses of solenopsin A and B have been developed which involve the Beckmann rearrangement-alkylation reaction promoted by organoaluminum reagents and a new stereoselective reduction of imino functional group. The recent discovery of the aluminum method for the direct synt