The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues

Organic Letters

Volumn 1, Issue 10, 1999, Pages 1647-1649

  Wang, Haishan ^a   Ganesan, A ^a,b  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011551580     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991030d     Document Type: Article

References (32)

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29. 1H NMR - the cis isomer has a more upfield chemical shift for the C1-methine in the tetrahydro-β-carboline ring. The cis/trans ratio was calculated based on the isolated yield, or by NMR peak integration in cases where the two diastereomers were not completely separable by chromatography. In all but two of the entries in Tables 1 and 2, the cis compound is more polar than the trans by TLC.
30. By NMR, we also detected approximately 10% of an epimeric pair of products, due to racemization of the tryptophan imine.
31. 2 (x5), and MeOH (x5)], and drying before use in the next step.
32. 2. Two major bands were seen, corresponding to cis and trans tetrahydro-β-carboline products, and collected.