Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-LundurineA

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

Research output: Contribution to journalArticle

5 Citations (Scopus)

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 (±)-lundurineA.

Original languageEnglish (US)
JournalAngewandte Chemie - International Edition
DOIs
StateAccepted/In press - Jan 1 2018

Fingerprint

Cyclization
Alkaloids
Carbon
indole

Keywords

  • Alkaloids
  • Cyclization
  • Lewis acids
  • Nitrogen heterocycles
  • Total synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-LundurineA. / Nash, Aaron; Qi, Xiangbing; Maity, Pradip; Owens, Kyle; Tambar, Uttam K.

In: Angewandte Chemie - International Edition, 01.01.2018.

Research output: Contribution to journalArticle

@article{2713f14206ab43eda5a111fa879cd752,
title = "Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-LundurineA",
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 (±)-lundurineA.",
keywords = "Alkaloids, Cyclization, Lewis acids, Nitrogen heterocycles, Total synthesis",
author = "Aaron Nash and Xiangbing Qi and Pradip Maity and Kyle Owens and Tambar, {Uttam K.}",
year = "2018",
month = "1",
day = "1",
doi = "10.1002/anie.201803702",
language = "English (US)",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",

}

TY - JOUR

T1 - Development of the Vinylogous Pictet-Spengler Cyclization and Total Synthesis of (±)-LundurineA

AU - Nash, Aaron

AU - Qi, Xiangbing

AU - Maity, Pradip

AU - Owens, Kyle

AU - Tambar, Uttam K.

PY - 2018/1/1

Y1 - 2018/1/1

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 (±)-lundurineA.

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 (±)-lundurineA.

KW - Alkaloids

KW - Cyclization

KW - Lewis acids

KW - Nitrogen heterocycles

KW - Total synthesis

UR - http://www.scopus.com/inward/record.url?scp=85046367349&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85046367349&partnerID=8YFLogxK

U2 - 10.1002/anie.201803702

DO - 10.1002/anie.201803702

M3 - Article

C2 - 29663602

AN - SCOPUS:85046367349

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

ER -