Total synthesis of the potent cAMP signaling agonist (-)-alotaketal A.

Journal of the American Chemical Society
Jinhua HuangJiong Yang

Abstract

We have developed a convergent synthetic route to the potent cAMP signaling agonist (-)-alotaketal A that employs two stages of SmI(2)-mediated reductive allylation reactions for assembling the polycycle and fragment coupling. Also notable are a Hg(OAc)(2)-mediated selective alkene oxidation and the subtlety of the formation of the unprecedented spiroketal ring system. The probes AKAR4 and ICUE3 were used to evaluate the cAMP singaling agonistic activity of (-)-alotaketal A and elucidate its structure-activity relationship.

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Citations

Jul 22, 2015·Organic Letters·GuangRong Peh, Paul E Floreancig
Oct 22, 2016·The Journal of Organic Chemistry·Meng WangRaymond J Andersen
Apr 4, 2017·Angewandte Chemie·Wei ZhangRongbiao Tong
Jul 7, 2017·Organic Letters·Seewon JoungHee-Yoon Lee
Mar 17, 2018·Natural Product Reports·Harry J ShirleyChristopher D Bray
Aug 25, 2018·Organic & Biomolecular Chemistry·Saumitra Sengupta, Goverdhan Mehta
Sep 15, 2018·Natural Product Reports·Yuye ChenJing Xu
Jul 11, 2019·Organic & Biomolecular Chemistry·Harry J Shirley, Christopher D Bray
Jan 7, 2014·Natural Product Reports·John W BluntMichèle R Prinsep
Oct 26, 2012·Organic Letters·Mengyang XuanStephen M Dalby
Apr 25, 2014·Chemical Reviews·Michal SzostakDavid J Procter
Feb 7, 2015·The Journal of Organic Chemistry·Jonathan G HubertMargaret A Brimble
Oct 27, 2020·Organic Letters·Balasaheb R BoradeRavindar Kontham

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