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

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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… Click to show full 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.

Keywords: cross dehydrogenative; free cross; total synthesis; cross; metal free

Journal Title: Chemical communications
Year Published: 2020

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