Transformation of Substituted Glycals to Chiral Fused Aromatic Cores via Annulative π-Extension Reactions with Arynes

Organic Letters
Nazar HussainDebaraj Mukherjee

Abstract

The Diels-Alder addition of arynes to appropriately substituted vinyl/aryl glycals followed by π-extension via pyran ring opening smoothly furnished meta-disubstituted fused aromatic cores containing a stereodefined orthogonally protected chiral side chain. The method is broad in terms of aryl homologation, affording benzene, naphthalene, and phenanthrene derivatives. Base-induced deprotonation followed by cleavage of the allylic C-O bond appear to be the crucial steps leading to the development of aromaticity, which is the driving force behind the annulative π-extension process. The present protocol can be used for the synthesis of meta-disubstituted naphthalene aldehydes and substrates for aldolases.

References

Apr 1, 1982·The Journal of Antibiotics·T T WeiM Greenstein
Nov 30, 2007·Angewandte Chemie·John E Anthony
Jan 4, 2008·Journal of the American Chemical Society·Eilaf AhmedSamson A Jenekhe
Oct 7, 2008·Organic Letters·Debaraj MukherjeeSubhash Chandra Taneja
Feb 27, 2009·Journal of the American Chemical Society·Irvinder KaurGlen P Miller
Jan 20, 2011·Organic Letters·Syed Khalid YousufSubhash C Taneja
Oct 14, 2014·Journal of the American Chemical Society·Emily J TollefsonElizabeth R Jarvo

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Related Concepts

Related Feeds

Allogenic & Autologous Therapies

Allogenic therapies are generated in large batches from unrelated donor tissues such as bone marrow. In contrast, autologous therapies are manufactures as a single lot from the patient being treated. Here is the latest research on allogenic and autologous therapies.