Total synthesis of exiguamines A and B inspired by catecholamine chemistry

Vladimir Sofiyev; Jean Philip Lumb; Matthew Volgraf; Dirk Trauner

doi:10.1002/chem.201103605

Total synthesis of exiguamines A and B inspired by catecholamine chemistry

Vladimir Sofiyev, Jean Philip Lumb, Matthew Volgraf, Dirk Trauner

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

The evolution of a total synthesis of the exiguamines, two structurally unusual natural products that are highly active inhibitors of indolamine-2,3-dioxygenase (IDO), is described. The ultimately successful strategy involves advanced cross-coupling methodology and features a potentially biosynthetic tautomerization/electrocyclization cascade reaction that forms two heterocycles and installs a quaternary ammonium ion in a single synthetic operation.

Original language	English (US)
Pages (from-to)	4999-5005
Number of pages	7
Journal	Chemistry - A European Journal
Volume	18
Issue number	16
DOIs	https://doi.org/10.1002/chem.201103605
State	Published - Apr 16 2012

Keywords

biomimetic synthesis
cross-coupling
dopamines
electrocyclic reactions
total synthesis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.201103605

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AU - Lumb, Jean Philip

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AU - Trauner, Dirk

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KW - cross-coupling

KW - dopamines

KW - electrocyclic reactions

KW - total synthesis

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Total synthesis of exiguamines A and B inspired by catecholamine chemistry

Abstract

Keywords

ASJC Scopus subject areas

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