PMID: 11929250Apr 4, 2002Paper

Stereoselective synthesis of tetrahydrofurans via formal [3+2]-cycloaddition of aldehydes and allylsilanes. Formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine

Journal of the American Chemical Society
Steven R Angle, Nahla A El-Said

Abstract

The stereoselective synthesis of tetrahydrofurans was achieved by formal [3+2]-cycloaddition of allyl and crotylsilanes with alpha-triethylsilyloxy aldehydes. The scope of the reaction was examined by using different alpha-substituted aldehydes and different substituents on the silicon. Tamao oxidation of the products resulted in formation of diols that are easily functionalized allowing an entry to natural products synthesis. The formal total synthesis of the muscarine alkaloids (-)-allomuscarine and (+)-epimuscarine was achieved.

References

Feb 7, 2001·Organic Letters·W R Roush, L A Pfeifer
Feb 19, 2002·Chemical Reviews·Ian FlemingDavid Walter

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Citations

Jun 28, 2005·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Liu FengyiWang Dianxun
Aug 22, 2009·Angewandte Chemie·Susan C WilkinsonVéronique Gouverneur
Jun 17, 2015·Angewandte Chemie·Zachary D MillerJohn Montgomery
Oct 19, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Yumiko NakajimaShigeru Shimada
Jul 24, 2008·The Journal of Organic Chemistry·Steven R AngleFook S Tham
Mar 5, 2015·The Journal of Organic Chemistry·Jihoon Lee, James S Panek
Jan 13, 2012·The Journal of Organic Chemistry·Mark G McLaughlin, Matthew J Cook
Feb 25, 2006·The Journal of Organic Chemistry·M Antonietta LoretoP Antonio Tardella

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