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).
A short and stereoselective synthesis of the (±) Prelog-Djerassi lactonic acid
✍ Scribed by Kazuhiro Maruyama; Yuji Ishihara; Yoshinori Yamamoto
- Publisher
- Elsevier Science
- Year
- 1981
- Tongue
- French
- Weight
- 225 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
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
## Levoglucosenone (1) was used as the starting material for short and stereoselective routes to chiral synthons for (-)d-multistriatin (2) and (+)-Prelog-Djerassi lactonic acid (3). The stereochemistry of these synthons is discussed on the basis of high-resolution 'H-n.m.r. data.