175398-33-1Relevant academic research and scientific papers
A new catalytic oxidative cleavage reaction to furnish lactones
Roth, Stefanie,Stark, Christian B. W.
, p. 6411 - 6413 (2008)
A highly efficient oxidative cleavage reaction of THF and THP alcohols to ?3- and ??-lactones using catalytic PCC (1 mol%) and periodic acid as terminal oxidant is presented. ? The Royal Society of Chemistry 2008.
Total Synthesis of (R)-Argentilactone and (R)-Goniothalamin Using a Free-Radical Photoredox Approach to α,β-Unsaturated δ-Lactones
Fuentes-Pantoja, Francisco J.,Cordero-Vargas, Alejandro
, p. 4433 - 4439 (2021/08/20)
α,β-Unsaturated δ-lactones are structural motifs found in diverse pharmacologically active natural products. In fact, the unsaturated lactone is often responsible for the biological activity. Herein, we report a new approach for the syntheses of (R)-argentilactone and (R)- goniothalamin based on a photoredox intermolecular iodolactonization mediated by a photoredox process. This new approach, already employed in our research group, stands as a new methodology to achieve several natural products containing α,β-Unsaturated δ-lactones.
Total synthesis of (-)-histrionicotoxin 285A and (-)- perhydrohistrionicotoxin
Macdonald, James M.,Horsley, Helen T.,Ryan, John H.,Saubern, Simon,Holmes, Andrew B.
supporting information; experimental part, p. 4227 - 4229 (2009/06/06)
(Chemical Equation Presented) Starting from commercially available (S)-glycidol, and via a common intermediate, the total synthesis of (-)-histrionicotoxin 285A and (-)-perhydrohistrionicotoxin has been achieved. Key to this synthesis was the efficient co
Determination of the relative and absolute stereochemistry of fostriecin (CI-920)
Boger, Dale L.,Hikota, Masataka,Lewis, Bryan M.
, p. 1748 - 1753 (2007/10/03)
The absolute stereochemistry of fostriecin (1, CI-920), a potent antitumor antibiotic presently in Phase I clinical trials at NCI, was determined to be 5R,8R,9R,11R. 2D 1H-1H NMR NOE experiments conducted on the cyclic phosphate derivative 2 and acetonide 4 revealed a syn-diol stereochemical relationship between C8 and C9 and an anti-diol stereochemical relationship between C9 and C11, respectively. The 5R absolute configuration assignment was confirmed by synthesis of the degradation product 8 previously disclosed. Additional degradation studies of 1 to provide 7 and chiral-phase HPLC comparison with a sample of known chirality established the absolute stereochemistry of C11 to be R. This, along with the relative stereochemical assignments established the full set of absolute stereochemistry assignments for 1.
A chemoenzymatic preparation of both enantiomers of ω-hydroxymethyl-substituted lactones
Buisson, Didier,Azerad, Robert
, p. 9 - 12 (2007/10/03)
(R)- and (S)-δ-hydroxymethyl valerolactone and ε-hydroxymethyl caprolactone were prepared as tert-butyldiphenylsilyl derivatives, in good yield and high enantiomeric purities, in a 5 step sequence, starting from the microbial stereospecific reduction of ethyl 2-oxocyclopentane or 2-oxocyclohexane carboxylates respectively.
