Synthesis and Structure of Preorganized, C3-Symmetric Trilactam Scaffolds with Convergently Oriented (S)-Acetylthiomethyl Appendages
- 1 June 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (13) , 2273-2275
- https://doi.org/10.1021/ol0261480
Abstract
Efficient modular synthesis of conformationally preorganized, C3-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Garner's l-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.Keywords
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