We thank the NIH (GM 069784) and the Welch Foundation (A-1280) for funding this work. We thank Kay Morris and Dr. Ziad Moussa, as well as Profs. Dan Singleton and Brian Connell for helpful discussions.
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Communication
Highly Diastereoselective, Tandem, Three-Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β-Lactone Intermediates†
Article first published online: 27 MAY 2008
DOI: 10.1002/anie.200800235
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Mitchell, T., Zhao, C. and Romo, D. (2008), Highly Diastereoselective, Tandem, Three-Component Synthesis of Tetrahydrofurans from Ketoaldehydes via Silylated β-Lactone Intermediates. Angewandte Chemie International Edition, 47: 5026–5029. doi: 10.1002/anie.200800235
- †
Publication History
- Issue published online: 16 JUN 2008
- Article first published online: 27 MAY 2008
- Manuscript Received: 16 JAN 2008
Funded by
- NIH. Grant Number: GM 069784
- Welch Foundation. Grant Number: A-1280
Keywords:
- cyclization;
- Mukaiyama aldol;
- oxocarbenium ions;
- synthetic methods;
- tandem reactions
Graphical Abstract
Like falling dominoes! A novel tandem, three-component reaction is described that generates up to two C![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
C bonds, one CO bond, and three additional stereocenters leading to substituted tetrahydrofuran units. This process involves a tandem Mukaiyama aldol-lactonization/reductive cyclization and proceeds via a silylated β-lactone intermediate. The method was applied to prepare the tetrahydrofuran fragment of colopsinol B. Py=2-pyridyl.