Journal
ORGANIC LETTERS
Volume 4, Issue 14, Pages 2337-2340Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol026015e
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Funding
- NIGMS NIH HHS [R01 GM054523-06, GM54523] Funding Source: Medline
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[GRAPHICS] 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.
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