Application of enzymatic methods to the synthesis of 5-substituted-2-furanones
β Scribed by Mukund P. Sibi; Janet A. Gaboury
- Publisher
- Elsevier Science
- Year
- 1992
- Tongue
- French
- Weight
- 312 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0040-4039
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π SIMILAR VOLUMES
Hypervalent iodine oxidation of Z-(trimethylsilyloxy)furan with iodosobenzeneboron bifluoride etherate in the presence of various nucleophiles yields 5-substituted-2(.5H)-furanones. 5Substituted-2(5H)-furanones are versatile intermediates for the synthesis of a number of important natural products a
## 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.
The adducts of a stereoselective radical addition of tertiary amines with (5R)-5-menthyloxy-2[5H]-furanone were transformed very efficiently into enantiomerically pure pyrrolizidine and indolizidine alkaloids, through a three steps sequence.