This research was supported in part by a Grant-in-Aid for Young Scientists (B, KAKENHI no. 22790022) from the Japan Society for the Promotion of Science. We thank Prof. K. Miyamura and K. Ueji (Department of Chemistry, Tokyo University of Science) for assistance with X-ray analysis.
A Synthetic Study of Atropurpuran: Construction of a Pentacyclic Framework by an Intramolecular Reverse-Electron-Demand Diels–Alder Reaction†
Article first published online: 24 AUG 2011
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 50, Issue 39, pages 9177–9179, September 19, 2011
How to Cite
Suzuki, T., Sasaki, A., Egashira, N. and Kobayashi, S. (2011), A Synthetic Study of Atropurpuran: Construction of a Pentacyclic Framework by an Intramolecular Reverse-Electron-Demand Diels–Alder Reaction. Angew. Chem. Int. Ed., 50: 9177–9179. doi: 10.1002/anie.201103950
- Issue published online: 15 SEP 2011
- Article first published online: 24 AUG 2011
- Manuscript Received: 10 JUN 2011
- Grant-in-Aid for Young Scientists. Grant Number: 22790022
- Diels–Alder reaction;
- synthetic methods;
Masked talent: A tetracyclo[5.3.3.04,9.04,12]tridecane skeleton can be accessed by an intramolecular reverse-electron-demand Diels–Alder (REDDA) reaction of masked ortho-benzoquinone (MOB; see scheme). This reaction gives access to the pentacyclic framework of atropurpuran, and also enables the construction of other anti-Bredt and cage-like complex molecules.