Prev. Article Next Article Table of Contents

Communication

Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G

Supporting Info

Phil S. Baran* and Jeremy M. Richter

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037

J. Am. Chem. Soc., 2005, 127 (44), pp 15394–15396

DOI: 10.1021/ja056171r

Publication Date (Web): October 18, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pbaran@scripps.edu

Abstract

The first total syntheses of welwitindolinone A and the most complex members of the fischerindole family, fischerindoles I and G, are reported. Highlights of these short, protecting-group-free syntheses include the application of the recently developed direct indole−carbonyl coupling, a simple approach for installing the quaternary center with neighboring chlorine atom, a regioselective dehydrogenation/dehydration cascade to access fischerindole I, and a remarkably facile oxidative ring contraction to construct welwitindolinone A. An alternative biogenetic hypothesis, whose accuracy is suggested by the success of the current syntheses, is also put forth for this alkaloid family.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue November 09, 2005
Received September 8, 2005

Recommend & Share

Related Content

Direct Coupling of Indoles with Carbonyl Compounds: Short, Enantioselective, Gram-Scale Synthetic Entry into the Hapalindole and Fischerindole Alkaloid FamiliesJournal of the American Chemical Society
- Direct Coupling of Indoles with Carbonyl Compounds: Short, Enantioselective, Gram-Scale Synthetic Entry into the Hapalindole and Fischerindole Alkaloid Families
  Phil S. Baran and Jeremy M. Richter
  Journal of the American Chemical Society 2004 126 (24), pp 7450–7451
  Abstract: The invention of a method for the direct union of indoles and carbonyl compounds (ketones, amides, esters) is described. Using this new method, a short, enantioselective, gram-scale and protecting group-free synthetic entry to the fischerindole and ...
  Abstract | Full Text HTML | Hi-Res PDF
Total Synthesis of (±)-PsychotrimineJournal of the American Chemical Society
- Total Synthesis of (±)-Psychotrimine
  Timothy Newhouse and Phil S. Baran
  Journal of the American Chemical Society 2008 130 (33), pp 10886–10887
  Abstract: A new process for the union of anilines with tryptamine derivatives has been developed, furnishing C-3 quaternized pyrroloindoline architectures. This chemoselective coupling of a tryptamine with 1.2 equiv of 2-iodoaniline proceeds efficiently on a gram-...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Total Synthesis of (±)-Chartelline CJournal of the American Chemical Society
- Total Synthesis of (±)-Chartelline C
  Phil S. Baran and Ryan A. Shenvi
  Journal of the American Chemical Society 2006 128 (43), pp 14028–14029
  Abstract: The first total synthesis of (±)-chartelline C in a concise 10-step sequence is reported. Highlights of the completion of this decades-old puzzle include (1) chemo- and position-selective installation of the heteroaromatic halogens, (2) halogen-sparing ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Enantioselective Total Syntheses of Welwitindolinone A and Fischerindoles I and G

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Direct Coupling of Indoles with Carbonyl Compounds: Short, Enantioselective, Gram-Scale Synthetic Entry into the Hapalindole and Fischerindole Alkaloid Families

Total Synthesis of (±)-Psychotrimine

Total Synthesis of (±)-Chartelline C

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES