A synthesis of (+)-Prelog-Djerassi Lactonic acid
β Scribed by Steven D. Hiscock; Peter B. Hitchcock; Philip J. Parsons
- Publisher
- Elsevier Science
- Year
- 1998
- Tongue
- French
- Weight
- 852 KB
- Volume
- 54
- Category
- Article
- ISSN
- 0040-4020
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β¦ Synopsis
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).
π SIMILAR VOLUMES
The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from Npropionylbornanesultam ent-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6 ---) 7) followed by saponification of the sultam moiety (7 --
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