Issue 27, 2021

TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline

Abstract

Multi-reactive centered reagents are beneficial in chemical synthesis due to their advantage of minimal material utilization and formation of less by-products. Trichloroisocyanuric acid (TCCA), a reagent with three reactive centers, was employed in the synthesis of spirooxindoles through the oxidative rearrangement of various N-protected tetrahydro-β-carbolines. In this protocol, low equivalents of TCCA were required to access spirooxindoles (up to 99% yield) with a wide substrate scope. Furthermore, the applicability and robustness of this protocol were proven for the gram-scale total synthesis of natural alkaloids such as (±)-coerulescine (1) and (±)-horsfiline (2) in excellent yields.

Graphical abstract: TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline

Supplementary files

Article information

Article type
Paper
Submitted
25 Mar 2021
Accepted
15 Apr 2021
First published
05 May 2021
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2021,11, 16537-16546

TCCA-mediated oxidative rearrangement of tetrahydro-β-carbolines: facile access to spirooxindoles and the total synthesis of (±)-coerulescine and (±)-horsfiline

M. Sathish, A. P. Sakla, F. M. Nachtigall, L. S. Santos and N. Shankaraiah, RSC Adv., 2021, 11, 16537 DOI: 10.1039/D1RA02381K

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