Scaffold-directed traceless synthesis of tetrahydro-β- carbolinehydantoins

Chih Hau Chen, Chia Mao Chang, Hsia Yuan Chen, Jin Ji Lai, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticle

17 Scopus citations

Abstract

Pharmacologically interesting tetrahydro-β-carbolinehydantoins have been prepared through four-step traceless synthesis by a combinatorial approach. Two-arm PEG 1 (MW ≈ 4000) was used as a soluble polymer support and reacted with Fmoc-protected L-tryptophane 2 to form bis-ester 3. The resulting polymer-supported amino ester 3 was deprotected, and amino ester 4 underwent Pictet-Spengler reaction with varoius ketones to form tricyclic indoles S. The nucleophilic piperidine in the tricyclic indole reacted with isocyanate to generate the urea intermediates and simultaneously intramolecular cyclization to release the target compounds 7 from the support in good yields.

Original languageEnglish
Pages (from-to)618-626
Number of pages9
JournalJournal of Combinatorial Chemistry
Volume9
Issue number4
DOIs
StatePublished - 1 Jul 2007

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