Abstract
Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.
Original language | English |
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Pages (from-to) | 5082-5092 |
Number of pages | 11 |
Journal | Tetrahedron |
Volume | 70 |
Issue number | 34 |
DOIs | |
Publication status | Published - 26 Aug 2014 |
Keywords
- 1,2-Diaminopropanoic acids (DAPs)
- Azalanthionines
- Aziridine-2-carboxylates
- Lanthionine
- Ring-opening
- β-Methyl azalanthionines