Preparation of pilot library with tetrahydro-β-carboline alkaloid core skeleton using tandem intramolecular Pictet–Spengler cyclization
2006; Elsevier BV; Volume: 47; Issue: 38 Linguagem: Inglês
10.1016/j.tetlet.2006.07.051
ISSN1873-3581
AutoresSung‐Chan Lee, Soo Young Choi, Young Keun Chung, Seung Bum Park,
Tópico(s)Chemical synthesis and alkaloids
ResumoA solid phase strategy has been developed for the synthesis of tetrahydro-β-carboline alkaloid library. The key transformation is an acid-catalyzed tandem intramolecular Pictet–Spengler cyclization from l-tryptophan which forms acyl iminiums with synchronous cleavage of products from the acid-labile SASRIN™ solid support. A pilot library with two diversity points has been successfully synthesized in high purity to demonstrate this strategy.
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