Concerning the synthesis of the tedanolide C(13)-C(23) fragment via anti-aldol reaction

Organic Letters
Joshua R Dunetz, William R Roush

Abstract

Synthesis of C(13)-C(23) aldehyde 4, an important intermediate in a planned total synthesis of tedanolide, is described. The stereoselectivity of the key anti-aldol reaction of aldehyde 5 and ketone 6 (en route to 4) perfectly tracks the enantiomeric purity of 5. It is demonstrated that aldehyde 24, a precursor of 5, undergoes facile epimerization during a Swern oxidation and stabilized ylide olefination sequence.

References

Jan 9, 2003·Journal of the American Chemical Society·Amos B SmithAndrew P Degnan
May 28, 2004·Proceedings of the National Academy of Sciences of the United States of America·Amos B SmithAndrew P Degnan
Apr 28, 2005·Journal of the American Chemical Society·Lisa D JulianWilliam R Roush
Jul 29, 2005·Organic Letters·Cheon-Gyu ChoAmos B Smith
Oct 26, 2006·Journal of the American Chemical Society·Gunnar EhrlichMarkus Kalesse
Aug 7, 2007·Organic Letters·Michael E Jung, Dongwon Yoo
Aug 19, 2007·Journal of the American Chemical Society·Amos B Smith, Dongjoo Lee
Dec 11, 2007·Organic Letters·Michael E Jung, Ting-hu Zhang
Jan 1, 2008·Chemistry : a European Journal·Gunnar EhrlichMarkus Kalesse

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Citations

Nov 5, 2008·Journal of the American Chemical Society·Joshua R DunetzWilliam R Roush
May 25, 2016·Organic & Biomolecular Chemistry·Joana ZambranaFèlix Urpí
Mar 7, 2014·Natural Product Reports·Markus KalesseHai-Hua Lu
Mar 27, 2021·Chemistry : a European Journal·Daniel Lücke, Markus Kalesse

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