Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine

Xiangbing Qi; Hongli Bao; Uttam K. Tambar

doi:10.1021/ja203960b

Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine

Xiangbing Qi, Hongli Bao, Uttam K. Tambar

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Abstract

We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis- tryptamine.

Original language	English (US)
Pages (from-to)	10050-10053
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	26
DOIs	https://doi.org/10.1021/ja203960b
State	Published - Jul 6 2011

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine",

abstract = "We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis- tryptamine.",

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AB - We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2′-bis- tryptamine.

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Total synthesis of (±)-trigonoliimine C via oxidative rearrangement of an unsymmetrical bis-tryptamine

Abstract

ASJC Scopus subject areas

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