Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), γ-methyl-γ-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivities. We believe that this process takes place through the in situ generation of protoanemonin followed by a Prins reaction. Herein, we describe this discovery, along with substrate scope and preliminary mechanistic studies.
Munoz, Alberto,Murelli, Ryan P.
supporting information
p. 6779 - 6781,3
(2012/12/13)
Acid-mediated coupling of γ-hydroxybutenolides and aldehydes: Synthesis of a new class of spirocyclic ketal-lactones
In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf), γ-methyl-γ-hydroxybutenolide reacts with aromatic aldehydes to generate a new class of stereochemically rich spirocyclic ketal-lactones in good yields and with excellent stereoselectivi
Munoz, Alberto,Murelli, Ryan P.
supporting information
p. 6779 - 6781
(2013/01/15)
Assessment of the Active-Site Requirements of 5-Aminolaevulinic Acid Dehydratase: Evaluation of Substrate and Product Analogues as Competitive Inhibitors
The enzyme 5-aminolaevulinic acid dehydratase (ALAD) is resonsible for the synthesis of porphobilinogen (PBG) from two molecules of 5-aminolaevulinic acid (ALA).Porphobilinogen is an important committed intermediate in the biosynthesis of tetrapyrroles.Th
Lueoend, Rainer M.,Walker, Josef,Neier, Reinhard W.
p. 5005 - 5013
(2007/10/02)
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