Tetrahedron Letters p. 5987 - 5988 (1999)
Update date:2022-08-03
Topics:
Wessig, Pablo
A novel synthetic route to bicyclic β-turn dipeptides (BTD) is described. It starts with L-β-benzoylalanine 1, which is N-protected and coupled with proline esters yielding the dipeptides 3. Upon irradiation 3a-c undergo a cyclization to the indolizinones 4 in a highly stereoselective manner. 4a and 4c were converted into the N-protected BTD derivatives suited for peptide synthesis. The absolute configuration of products 4 and 5 were unambiguously elucidated from NOE results.
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