Prev. Article Next Article Table of Contents

Letter

Concise Synthesis of the Bicyclic Scaffold of N-Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization

Supporting Info

Xia Tian, Alexander D. Huters, Colin J. Douglas and Neil K. Garg*

Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569

Org. Lett., 2009, 11 (11), pp 2349–2351

DOI: 10.1021/ol9007684

Publication Date (Web): May 11, 2009

neilgarg@chem.ucla.edu

Abstract

A concise synthesis of the N-methylwelwitindolinone C isothiocyanate scaffold is disclosed. The approach relies on an indolyne cyclization to construct the [4.3.1]-bicyclic ring system present in the natural product. Subsequent oxidation of the indole core occurs with excellent diastereoselectivity to afford oxindole 2, the structure of which was confirmed by X-ray crystallographic analysis.

View: Full Text HTML | Hi-Res PDF | PDF w/ Links

Tools

SciFinder Links

Explore by:

Author of this Article Any Author Research Topic

History

Published In Issue June 04, 2009
Article ASAPMay 11, 2009
Received: April 09, 2009

Recommend & Share

Related Content

Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and SulfamatesJournal of the American Chemical Society
- Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates
  Kyle W. Quasdorf, Michelle Riener, Krastina V. Petrova and Neil K. Garg
  Journal of the American Chemical Society 2009 131 (49), pp 17748–17749
  Abstract: The first Suzuki−Miyaura cross-couplings of carbamates, carbonates, and sulfamates is described. The method provides a powerful means of using simple derivatives of phenol as precursors to polysubstituted aromatic compounds, as exemplified by a concise ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Indolynes as Electrophilic Indole Surrogates: Fundamental Reactivity and Synthetic ApplicationsOrganic Letters
- Indolynes as Electrophilic Indole Surrogates: Fundamental Reactivity and Synthetic Applications
  Sarah M. Bronner, Kevin B. Bahnck and Neil K. Garg
  Organic Letters 2009 11 (4), pp 1007–1010
  Abstract: A mild method to access a variety of substituted indole derivatives has been developed. The strategy relies on the generation of highly reactive indolyne intermediates, which function as electrophilic indole surrogates.
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
An Interrupted Fischer Indolization Approach toward Fused Indoline-Containing Natural ProductsOrganic Letters
- An Interrupted Fischer Indolization Approach toward Fused Indoline-Containing Natural Products
  Ben W. Boal, Alex W. Schammel and Neil K. Garg
  Organic Letters 2009 11 (15), pp 3458–3461
  Abstract: An efficient method to access the fused indoline ring system present in a multitude of bioactive molecules has been developed. The strategy involves the condensation of hydrazines with latent aldehydes to ultimately deliver indoline-containing products ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF

Letter

Concise Synthesis of the Bicyclic Scaffold of N-Methylwelwitindolinone C Isothiocyanate via an Indolyne Cyclization

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Suzuki−Miyaura Coupling of Aryl Carbamates, Carbonates, and Sulfamates

Indolynes as Electrophilic Indole Surrogates: Fundamental Reactivity and Synthetic Applications

An Interrupted Fischer Indolization Approach toward Fused Indoline-Containing Natural Products

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES