Total Synthesis of (−)-N-Methylwelwitindolinone C Isothiocyanate

We report the first total synthesis of (−)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bri...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2011-10, Vol.133 (40), p.15797-15799
Main Authors: Huters, Alexander D, Quasdorf, Kyle W, Styduhar, Evan D, Garg, Neil K
Format: Article
Language:English
Subjects:
Chemistry Techniques, Synthetic
Cyanobacteria - chemistry
Cyclization
Indole Alkaloids - chemical synthesis
Indoles - chemical synthesis
Indoles - chemistry
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We report the first total synthesis of (−)-N-methylwelwitindolinone C isothiocyanate. Our route features a number of key transformations, including an indolyne cyclization to assemble the [4.3.1]-bicyclic scaffold, as well as a late-stage intramolecular nitrene insertion to functionalize the C11 bridgehead carbon en route to the natural product.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja206538k