A convergent synthesis of the renin inhibitor SPP-100 using a nitrone intermediate
β Scribed by Alessandro Dondoni; Geert De Lathauwer; Daniela Perrone
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 74 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
The total synthesis of SPP-100 and its C-5 epimer involves the construction of the b-amino alcohol segment via addition of the Grignard reagent derived from 3-aryl-2-isopropyl-1-chloropropane to the nitrone functional group installed at C-4 of the pseudoephedrine spiroanellated g-butyrolactone derivative.
π SIMILAR VOLUMES
Pseudoephedrine serves as a dual purpose chiral auxiliary and protecting group in the synthesis of the novel orally active renin inhibitor CGP60536B.
We report a convergent synthesis of the potent orally active non-peptide renin inhibitor CGP60536B. The key reaction employs the coupling of the enantiopure Grignard species derived from chloride 13 with the diastereomerically pure g-lactone 9b. The stereoselective reduction of the resulting ketone
In 1962 "azapeptides" were described for the first time'). In these peptide analogs the a-CH group of one or more amino acid residues of a peptide chain is replaced with nitrogen.