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. 2021 May 5;11(27):16537-16546.
doi: 10.1039/d1ra02381k. eCollection 2021 Apr 30.

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

Manda Sathish  1   2 , Akash P Sakla  3 , Fabiane M Nachtigall  4 , Leonardo S Santos  2 , Nagula Shankaraiah  3
Affiliations

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

Manda Sathish et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Representative examples of bioactive spirooxindoles (1–4).
Fig. 2
Fig. 2. Comparison of present work with previous methods.
Scheme 1
Scheme 1. (A) Imine formation of N2 unprotected THBCs. (B) Plausible reaction mechanism for the oxidative rearrangement of N2-protected THBCs.
Scheme 2
Scheme 2. Gram-scale synthesis of (±)-coerulescine (1) and (±)-horsfiline (2).
See this image and copyright information in PMC

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