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Intramolecular Carbolithiation as a Route to a Sterically Congested Cyclopentene: Synthesis of the Longtailed Mealybug Pheromone

✍ Scribed by Bailey, William F.; Bakonyi, Johanna M.


Book ID
120077959
Publisher
American Chemical Society
Year
2013
Tongue
English
Weight
285 KB
Volume
78
Category
Article
ISSN
0022-3263

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Sodium borohydride-carbonyl reduction of the novel 3-(2-fluoro-5-nitro) phenyl-4-benzoyl-2-azetidinones 3 and 7 gave quantitatively the stereoisomeric carbinols (4R p ,5S p )-4 and (4R p ,5R p )-5. Treatment of the latter with sodium hydride gave the title compounds 8 and 9, respectively, with good