We are grateful for the financial support from the National Natural Science Foundation of China (21172150, 21021001), the National Basic Research Program of China (973 Program, 2010CB833200), and Sichuan University (Distinguished Young Scientist Program, 2011SCU04A18).
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Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6-cis-Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins†
Article first published online: 13 APR 2012
DOI: 10.1002/anie.201201323
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lu, J., Song, Z., Zhang, Y., Gan, Z. and Li, H. (2012), Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6-cis-Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins . Angew. Chem. Int. Ed., 51: 5367–5370. doi: 10.1002/anie.201201323
- †
Publication History
- Issue published online: 23 MAY 2012
- Article first published online: 13 APR 2012
- Manuscript Received: 17 FEB 2012
Funded by
- National Natural Science Foundation of China. Grant Numbers: 21172150, 21021001
- National Basic Research Program of China. Grant Number: 2010CB833200
- Sichuan University. Grant Number: 2011SCU04A18
Keywords:
- cyclizations;
- heterocycles;
- natural products;
- silanes;
- synthetic methods
Prins Charming: Prins cyclization of a bis(silyl) homoallylic alcohol with an aldehyde shows excellent cis and Z selectivity to form tetrahydropyrans containing a geometrically defined exocyclic vinylsilane. This reaction was used as the key step in the synthesis of ring B of the bryostatins.