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A synthesis of (+)-Prelog-Djerassi Lactonic acid

✍ 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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✦ 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).


πŸ“œ SIMILAR VOLUMES


Enantioselective synthesis of the Prelog
✍ Wolfgang Oppolzer; Eric Walther; Carlos PΓ©rez Balado; Jef De Brabander πŸ“‚ Article πŸ“… 1997 πŸ› Elsevier Science 🌐 French βš– 258 KB

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 --

Total synthesis of (+)-prelog-djerassi l
✍ Minoru Isobe; Yoshiyasu Ichikawa; Toshio Goto πŸ“‚ Article πŸ“… 1981 πŸ› Elsevier Science 🌐 French βš– 203 KB

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