Diastereoselective synthesis of the 5-hydroxy-pyrrolidinone amino acid of the microsclerodermins and model studies for an end-game strategy for microsclerodermin B

作者：Winter Christian; Pullin Robert D C; Donohoe Timothy J^*

来源：Tetrahedron Letters, 2017, 58(7): 602-605.

DOI：10.1016/j.tetlet.2016.12.045

• Amino acids
• Cyclic peptides
• Stereoselective synthesis
• Peptide coupling
• Metathesis

The first diastereoselective synthesis of the 5-hydroxy-pyrrolidinone amino acid common to eight members of the microsclerodermin family is presented. Our strategy involves formal hydration of an unsaturated precursor via the use of a two-step hydroxybromination-debromination protocol; this procedure provides exclusively the requisite 4,5-cis-pyrrolidinone. Furthermore model studies are presented that indicated the potential viability of this hydration strategy in the context of a synthesis of microsclerodermin B.

• 出版日期2017-2-15