Development of the Vinylogous Pictet–Spengler Cyclization and Total Synthesis of (±)-Lundurine A

Aaron Nash; Xiangbing Qi; Pradip Maity; Kyle Owens; Uttam K. Tambar

doi:10.1002/anie.201803702

Development of the Vinylogous Pictet–Spengler Cyclization and Total Synthesis of (±)-Lundurine A

Aaron Nash, Xiangbing Qi, Pradip Maity, Kyle Owens, Uttam K. Tambar

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

22 Scopus citations

Abstract

A novel vinylogous Pictet–Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A.

Original language	English (US)
Pages (from-to)	6888-6891
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	57
Issue number	23
DOIs	https://doi.org/10.1002/anie.201803702
State	Published - Jun 4 2018

Keywords

Lewis acids
alkaloids
cyclization
nitrogen heterocycles
total synthesis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.201803702

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title = "Development of the Vinylogous Pictet–Spengler Cyclization and Total Synthesis of (±)-Lundurine A",

abstract = "A novel vinylogous Pictet–Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A.",

keywords = "Lewis acids, alkaloids, cyclization, nitrogen heterocycles, total synthesis",

author = "Aaron Nash and Xiangbing Qi and Pradip Maity and Kyle Owens and Tambar, {Uttam K.}",

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doi = "10.1002/anie.201803702",

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T1 - Development of the Vinylogous Pictet–Spengler Cyclization and Total Synthesis of (±)-Lundurine A

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AU - Qi, Xiangbing

AU - Maity, Pradip

AU - Owens, Kyle

AU - Tambar, Uttam K.

N1 - Funding Information: Financial support was provided by a W. W. Caruth, Jr. Endowed Scholarship, the Welch Foundation (I-1748), the National Institutes of Health (R01GM102604), the National Science Foundation (1150875), and a Sloan Research Fellowship. Publisher Copyright: © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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N2 - A novel vinylogous Pictet–Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A.

AB - A novel vinylogous Pictet–Spengler cyclization has been developed for the generation of indole-annulated medium-sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)-lundurine A.

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KW - alkaloids

KW - cyclization

KW - nitrogen heterocycles

KW - total synthesis

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Development of the Vinylogous Pictet–Spengler Cyclization and Total Synthesis of (±)-Lundurine A

Abstract

Keywords

ASJC Scopus subject areas

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