Issue 6, 2021

Access to 1-indolyltetrahydro-β-carbolines via metal-free cross-dehydrogenative coupling: the total synthesis of eudistomin U, isoeudistomin U and 19-bromoisoeudistomin U

Abstract

A highly selective and captivating metal-free cross-dehydrogenative coupling for the cross-coupling of two reactive nucleophiles such as tetrahydro-β-carboline and indoles is developed. A series of 1-indolyltetrahydro-β-carboline derivatives were synthesized in excellent to moderate yields. Temperature, time and concentration control resulted in mono indolylation selectively. Moreover, the total synthesis of eudistomin U and isoeudistomin U and the first total synthesis of 19-bromoisoeudistomin U were accomplished.

Graphical abstract: Access to 1-indolyltetrahydro-β-carbolines via metal-free cross-dehydrogenative coupling: the total synthesis of eudistomin U, isoeudistomin U and 19-bromoisoeudistomin U

Supplementary files

Article information

Article type
Communication
Submitted
19 10 2020
Accepted
10 12 2020
First published
10 12 2020

Chem. Commun., 2021,57, 757-760

Access to 1-indolyltetrahydro-β-carbolines via metal-free cross-dehydrogenative coupling: the total synthesis of eudistomin U, isoeudistomin U and 19-bromoisoeudistomin U

G. Ranjani and R. Nagarajan, Chem. Commun., 2021, 57, 757 DOI: 10.1039/D0CC06958B

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