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A stereocontrolled synthesis of the (.+-.) Djerassi-Prelog lactonic acid

โœ Scribed by Stork, Gilbert; Nair, Vijay


Book ID
126202292
Publisher
American Chemical Society
Year
1979
Tongue
English
Weight
259 KB
Volume
101
Category
Article
ISSN
0002-7863

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๐Ÿ“œ SIMILAR VOLUMES


A synthesis of (+)-Prelog-Djerassi Lacto
โœ Steven D. Hiscock; Peter B. Hitchcock; Philip J. Parsons ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 852 KB

A new approach to the synthesis of Prelog-Djerassi Lactonic acid (1) is reported. A key step in this synthesis involves an lreland-Claisen rearrangement/silicon-mediated fragmentation sequence to provide the carbon framework in (1).

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Optically active Prelog-Djerassi Lactonic Acid i was synthesized from D-glucal; the crucial point being the elaboration of the carboxylic group as shown in eq. 1 and 2 which involve the sequential process [i] asymmetric addition of methyl anion onto the hetero-olefin 2, [ii] trapping