Synthesis of ?-Trimethylsilyloxythioethers and ?-Hydroxythioethers by the Reaction of Epoxides with Aryl- and Alkylthiotrimethylsilanes
- 1 January 1981
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 11 (5) , 391-398
- https://doi.org/10.1080/00397918108064305
Abstract
As part of our research into methods for the synthesis of leukotrienes (LTC4, LTD4, and LTE4)1, important natural mediators of allergic asthma, we have sought to develop mild and stereo-selective procedures for the preparation of complex β-hydroxythio-ethers. We have recently described the reaction of the S-trimethylsilyl derivative of N-trifluoroacetylglutathione dimethyl ester with the highly reactive epoxide, leukotriene A4, as a key step in the synthesis of LTC4 2. We now wish to report on the general synthetic utility and some mechanistic aspects of this novel reaction.Keywords
This publication has 12 references indexed in Scilit:
- The synthesis of a leukotriene with SRS-like activityTetrahedron Letters, 1980
- Slow Reacting Substances (SRSs): The structure identification of SRSs from rat basophil leukaemia (RBL-1) cellsProstaglandins, 1980
- Cleavage of methyl and benzyl ethers with thiotrimethylsilanesTetrahedron Letters, 1980
- Stepwise and selective dealkylation of phosphotriesters with phenylthiotrimethylsilaneTetrahedron Letters, 1979
- Characterization of the two major species of slow reacting substance from rat basophilic leukemia cells as glutathionyl thioethers of eicosatetraenoic acids oxygenated at the 5 position. Evidence that peroxy groups are present and important for spasmogenic activityProstaglandins, 1979
- Leukotriene C: a slow-reacting substance from murine mastocytoma cells.Proceedings of the National Academy of Sciences, 1979
- Hydroxysulfenylation of olefins. An olefin cleavage with functional group differentiationJournal of the American Chemical Society, 1978
- A facile synthesis of trimethylsilyl thioethersJournal of Organometallic Chemistry, 1973
- A novel route to silylthioethersJournal of Organometallic Chemistry, 1973
- The formation of alkoxysilanes from the interaction of linear and cyclic thiosilanes and disilthianes with oxygen heterocyclic ringsJ. Chem. Soc. A, 1968