Tetrahedron Letters p. 5217 - 5220 (1993)
Update date:2022-08-17
Topics:
Bohnstedt, Adolph C.
Prasad, J. V. N. Vara
Rich, Daniel H.
The synthesis of MeLeu and MeLeu-D-Leu alkene dipeptide isosteres are described. Isosteres with an E-alkene bond were synthesized stereoselectively by employing the [2, 3] Wittig rearrangement to control double bond geometry and C-2 configuration. Z-alkene isosters were obtained as an easily separable mixture of diastereomers via alkylation of a Z-alkene MeLeu-Gly isostere that was obtained using a Z-selective Wittig reaction as the key step. All isosteres are isolated with high stereochemical purity.
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