Inversion of configurations of contiguous carbinol centres: application to the synthesis of both enantiomers of natural products from the same enantiomerically pure starting material
✍ Scribed by Petpiboon Prasit; Gilles Robertson; Joshua Rokach
- Publisher
- Elsevier Science
- Year
- 1990
- Tongue
- English
- Weight
- 854 KB
- Volume
- 202
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
A novel method for effecting the inversion of configuration of two and three contiguous carbinol centers in a diol, trial, and tetraol chain, thus affording the opposite enantiomer with > 98% e.e., has been developed. The method is based on the sequential formation of a terminal epoxide, Payne rearrangement, and intramolecular lactonization. Application of this methodology to the synthesis of a leukotriene A4 intermediate and its enantiomer, and the oviposition attractant pheromone of the mosquito Culex pipiens fatiguns and its enantiomer, from the same enantiomerically pure starting material is described'.