ChemInform Abstract: Convergent and Short-Step Syntheses of dl-Cypridina Luciferin and Its Analogues Based on Pd-Mediated Cross Couplings.

dl-Cypridina luciferin and its analogues were synthesized from 2-aminopyrazine by an eight-step method that included two regio-selective Pd-mediated cross couplings, and their chemi- and bioluminescent activities were compared. Analogues having a 3-benzofuranyl or a 3-benzothienyl group in the place of a 3-indolyl group showed luciferase affinities similar to Cypridina luciferase but with a lower luminescent efficiency, suggesting that the NH group is unimportant for molecular recognition whereas the indolyl group is crucial for efficient luminescence. (C) 2000 Elsevier Science Ltd. All rights reserved.