Stereocontrolled Synthesis of Spiroketals: An Engine for Chemical and Biological Discovery

Israel Journal of Chemistry
Alyssa L Verano, Derek S Tan

Abstract

Spiroketals are key structural motifs found in diverse natural products with compelling biological activities. However, stereocontrolled synthetic access to spiroketals, independent of their inherent thermodynamic preferences, is a classical challenge in organic synthesis that has limited in-depth biological exploration of this intriguing class. Herein, we review our laboratory's efforts to advance the glycal epoxide approach to the stereocontrolled synthesis of spiroketals via kinetically controlled spirocyclization reactions. This work has provided new synthetic methodologies with applications in both diversity- and target-oriented synthesis, fundamental insights into structure and reactivity, and efficient access to spiroketal libraries and natural products for biological evaluation.

References

Sep 12, 1997·The Journal of Biological Chemistry·M K LindvallA M Koskinen
May 10, 2002·Organic Letters·Guy D Joly, Eric N Jacobsen
Jul 4, 2002·Journal of the American Chemical Society·James W A KinnairdJames L Leighton
Aug 17, 2002·Bioorganic & Medicinal Chemistry Letters·Eileen M SewardBrian J Williams
Jan 22, 2004·Chemistry : a European Journal·Tobias C WabnitzJonathan B Spencer
Jan 13, 2005·Journal of the American Chemical Society·Leo R TakaokaScott D Rychnovsky
Apr 23, 2005·Organic Letters·Christine M DiblasiDerek S Tan
Oct 6, 2005·Journal of the American Chemical Society·Justin S PotuzakDerek S Tan
Mar 23, 2006·Journal of the American Chemical Society·Syed Alipayam RizviSergey A Kozmin
Sep 1, 2007·Science·Ivan Vilotijevic, Timothy F Jamison
Jan 16, 2008·The Journal of Organic Chemistry·Hassina HarkatPatrick Pale
Apr 24, 2009·Journal of the American Chemical Society·Jeffery A Byers, Timothy F Jamison
May 1, 2009·Journal of the American Chemical Society·Christopher J Morten, Timothy F Jamison
Jul 8, 2010·Chemical & Pharmaceutical Bulletin·Juan-Li GuoPei-Cheng Zhang
Jul 22, 2010·Natural Product Reports·Jonathan SperryMargaret A Brimble
Jan 18, 2011·Journal of the American Chemical Society·Christopher J MortenTimothy F Jamison
Oct 1, 2011·Organic Letters·Gangarajula SudhakarBharatam Jagadeesh
Oct 21, 2011·The Journal of Organic Chemistry·Tuan Thanh DangLukas Hintermann
Aug 29, 2012·Organic Letters·Jacqueline M WurstDerek S Tan
Sep 25, 2012·The Journal of Organic Chemistry·Nicholas V Borrero, Aaron Aponick
Mar 9, 2013·Bioscience, Biotechnology, and Biochemistry·Takaaki TeranishiShigefumi Kuwahara
Jun 26, 2013·Food Chemistry·Deshou Jiang, Devin G Peterson
Sep 21, 2013·Proceedings of the National Academy of Sciences of the United States of America·Jeffery A Byers, Timothy F Jamison
Aug 20, 2014·Organic & Biomolecular Chemistry·Rachelle QuachMargaret A Brimble
Jul 15, 2015·Journal of Asian Natural Products Research·Bo DingXin-Sheng Yao

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Citations

Jan 9, 2019·Organic & Biomolecular Chemistry·Elena LenciAndrea Trabocchi
Oct 22, 2021·The Journal of Organic Chemistry·Kimberly M Hilby, Scott E Denmark

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