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

Jinhua Huang, Jessica R. Yang, Jin Zhang, Jiong Yang

Research output: Contribution to journalArticle

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.

Original languageEnglish (US)
Pages (from-to)8806-8809
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number21
DOIs
StatePublished - May 30 2012

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Allylation
Olefins
Oxidation
Alkenes
Structure-Activity Relationship
alotaketal A

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Total synthesis of the potent cAMP signaling agonist (-)-Alotaketal A. / Huang, Jinhua; Yang, Jessica R.; Zhang, Jin; Yang, Jiong.

In: Journal of the American Chemical Society, Vol. 134, No. 21, 30.05.2012, p. 8806-8809.

Research output: Contribution to journalArticle

Huang, Jinhua ; Yang, Jessica R. ; Zhang, Jin ; Yang, Jiong. / Total synthesis of the potent cAMP signaling agonist (-)-Alotaketal A. In: Journal of the American Chemical Society. 2012 ; Vol. 134, No. 21. pp. 8806-8809.
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