Synthesis of a C3-symmetric nanoscale molecular platform based on marine cyclopeptides.

In: Synlett, (2004) ; Nr. 6, S. 1003-1006
ISSN: 0936-5214
Zeitschriftenaufsatz / Fach: Chemie
Efficient synthesis of a conformationally preorganized, C3-sym. mol. platform is reported. The rigid scaffold is based on the structure of marine cyclopeptides and presents three functional groups pointing in the same direction. For example, bicyclic imidazole I (TBS = SiMe2Bu-t) was synthesized in seven steps from trans-4-hydroxy-(S)-proline Me ester. I was converted into TBS-protected macrocycle II (R = SiMe2Bu-t) in two steps, followed by deprotection to give hydroxy deriv. II (R = H). Similarly, dimethylimidazole-based macrocycles (R = H, CHMe2, CH2Ph, CH2NHCbz) were prepd.