Use of azalactones in a 'Pictet-Spengler-like' reaction. Stereoselective synthesis of 1,3,4-substituted tetrahydro-β-carbolines

DOI: 10.1016/0040-4039(96)01233-6

Source and publish data:

Tetrahedron Letters p. 5813 - 5816 (1996)

Update date:2022-08-12

Topics:

Authors:

Ezquerra, Jesus

Lamas, Carlos

Pastor, Alfredo

Alvarez, Pilar

Vaquero, Juan Jose

Prowse, Will G.

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Article abstract of DOI:10.1016/0040-4039(96)01233-6

A 'Pictet-Spengler-like' reaction between azalactones 1 and conformationally constrained tryptamines 4 in refluxing 1N HCl over 72 h. gave the corresponding tetrahydro-β-carbolines 3 in moderate to good yields. The observed equatorial orientation of the C-1 substituent in the THBC's results from a combination of the thermal reaction conditions and conformational constraints imposed by the starting tryptamines.

Full text of DOI:10.1016/0040-4039(96)01233-6

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