Enantiospecific Synthesis of Natural (−)-Cocaine and Unnatural (+)-Cocaine from d - and l -Glutamic Acid
✍ Scribed by Lin, Ronghui; Castells, Josep; Rapoport, Henry
- Book ID
- 118259456
- Publisher
- American Chemical Society
- Year
- 1998
- Tongue
- English
- Weight
- 131 KB
- Volume
- 63
- Category
- Article
- ISSN
- 0022-3263
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📜 SIMILAR VOLUMES
An enantiospeci!ic route to jasmonoid natural products, (+) -methyl epijasmonate and (-) -methyl cucmbate from L-glutamic acid is reported. The key step is a 5-(3,4) ene cyclization of a fmxtionahzed 14diene as chiron. which sets up three chin11 centres with a high degree of diastereoselectivity.
L-Glutamic acid has been converted into a separable mixture of D-amicetonoand L-rhodinono-y-lactones by a sequence involving transformation into (S)-y-carboxy-y-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohyd