Synthesis of (+/-)-madindolines and chemical models. Studies of chemical reactivity.

Autor: McComas CC; Department of Chemistry, University of California, Irvine, California 92697-2025, USA., Perales JB, Van Vranken DL
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2002 Jul 11; Vol. 4 (14), pp. 2337-40.
DOI: 10.1021/ol026015e
Abstrakt: [reaction: see text] The madindolines are believed to inhibit cytokine signaling through the gp130 receptor. Model compounds of madindolines were synthesized and tested for thiol reactivity. The heterocyclic moiety of madindoline was shown to form thiol adducts via the Savige-Fontana reaction. The enedione moiety was found to be unreactive toward simple thiols unless the quaternary center was removed. Using the powerful Moore reaction, we have synthesized (+/-)-madindoline A and B in 11 steps.
Databáze: MEDLINE