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Synthesis of diverse tetrahydro-β-carboline-3-carboxamides and -2,3-bis-lactams on a versatile 4-hydroxythiophenol-linked solid support

✍ Scribed by Pascal P. Fantauzzi; Kraig M. Yager

Book ID: 104258709
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 333 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10869-3

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✦ Synopsis

A practical method for solid phase organic synthesis has been developed using the known, but heretofore underutilized, 4-hydroxythiophenol linker of Marshall and Liener. The utility of this linker is demonstrated by the synthesis of 1,2,3,4-tetrahydro-8-carboline-3carboxamides and -2,3-bis-lactams. Acylation of the resin with L-Boc-tryptophan followed by deprotection and Pictet-Spengler cyclization with a variety of aldehydes provided tetrahydroj3carbolines with excellent conversion.

Cleavage from the resin with primary amines provided the amides and an additional diversity element. Alternatively, acylation at the carboline P-position with Boc-protected a-or p-amino acid derivatives followed by deprotection and neutralization resulted in intramolecular cyclization and cleavage to afford 6-and 7-membered bis-lactams.

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