Issue 22, 2023

Total synthesis of aspidostomide G from a brominated tryptamine

Abstract

The first total synthesis of aspidostomide G using a brominated tryptamine is described. The synthetic route features several notable aspects: (a) the starting material, compound 13, contains a built-in hydroxy group and was transformed to the Sonogashira reaction precursor; (b) the construction of the indole ring was achieved through a transition-metal catalyzed synthesis and a 5-endo-dig cyclization. The desired indole 9 was synthesized in only 7 steps with an overall yield of 54% and required only three columns; (c) a late C2-bromination was achieved by using the 4-acetoxyindole analogue 14c.

Graphical abstract: Total synthesis of aspidostomide G from a brominated tryptamine

Supplementary files

Article information

Article type
Communication
Submitted
30 Apr 2023
Accepted
17 May 2023
First published
17 May 2023

Org. Biomol. Chem., 2023,21, 4601-4605

Total synthesis of aspidostomide G from a brominated tryptamine

B. Wu, F. Shih, Y. Tsai, C. Chu and C. Lin, Org. Biomol. Chem., 2023, 21, 4601 DOI: 10.1039/D3OB00672G

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