Synthesis using Suzuki cross couplings of sulfur analogues of dehydrotryptophan with a definite stereochemistry

…, AS Abreu, PMT Ferreira, LS Monteiro…

Index: Silva, Natalia O.; Abreu, Ana S.; Ferreira, Paula M. T.; Monteiro, Luis S.; Queiroz, Maria-Joao R. P. European Journal of Organic Chemistry, 2002 , # 15 p. 2524 - 2528

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Citation Number: 24

Abstract

Abstract Sulfur analogues of dehydrotryptophan (5− 7) were prepared in moderate to good yields (40− 80%) by Suzuki cross coupling [Pd (PPh 3) 4, Na 2 CO 3 or NaHCO 3, DME/H 2 O, 90 C] of several benzo [b] thiophene boronic acids with the methyl esters of N-tert- butyloxycarbonyl-β-bromodehydroalanine [Boc-ΔAla (β-Br)-OMe] or N-tert-butyloxycarbonyl- β-bromodehydroaminobutyric acid [Boc-ΔAbu (β-Br)-OMe]. The β-bromodehydroamino ...