+)-Muscarine has been synthesized from (S)-(-)-5-hydroxy-2(5H)-furanone via rather a long pathway to provide easy access to a wide variety of its analogues.
An efficient synthesis of (S)-5-hydroxymethyl-2(5H)-furanone
β Scribed by Jozef A.J.M Vekemans; Gabriel A.M Franken; Gordon J.F Chittenden; Erik F Godefroi
- Book ID
- 108382938
- Publisher
- Elsevier Science
- Year
- 1987
- Tongue
- French
- Weight
- 109 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
## Abstract Highly optically active 4βsubstitutedβ2(5__H__)βfuranones 6aβ6j were obtained in good yields with __de__β©Ύ98% by the tandem Michael addition/elimination reaction of chiral 3βbromoβ2(5__H__)βfuranone (4a), which was conveniently prepared starting from 2βfuraldehyde under mild conditions.
Starting fro enolizing 1.2~diketones 1 and (2,2dlathoxyvinylidene)triphenylphosphorane (1) or from 2 and (2.2-dlethoxyvlnyl)triphewlphosphonlu tetrafluorohorate (a) the orthoesters 2 are prepared. 9 can be hydrolyzed under acldlc conditions to glve 5-alkylldene-2(SH)-furan%es lo. Reaction of 1,2-hyd