113089-15-9Relevant articles and documents
Chemical and Genetic Studies on the Formation of Pyrrolones During the Biosynthesis of Cytochalasans
Zhang, Haili,Hantke, Verena,Bruhnke, Pia,Skellam, Elizabeth J.,Cox, Russell J.
, p. 3106 - 3113 (2021/01/20)
A key step during the biosynthesis of cytochalasans is a proposed Knoevenagel condensation to form the pyrrolone core, enabling the subsequent 4+2 cycloaddition reaction that results in the characteristic octahydroisoindolone motif of all cytochalasans. In this work, we investigate the role of the highly conserved α,β-hydrolase enzymes PyiE and ORFZ during the biosynthesis of pyrichalasin H and the ACE1 metabolite, respectively, using gene knockout and complementation techniques. Using synthetic aldehyde models we demonstrate that the Knoevenagel condensation proceeds spontaneously but results in the 1,3-dihydro-2H-pyrrol-2-one tautomer, rather than the required 1,5-dihydro-2H-pyrrol-2-one tautomer. Taken together our results suggest that the α,β-hydrolase enzymes are essential for first ring cyclisation, but the precise nature of the intermediates remains to be determined.
Possible origin of electronic effects in Rh(I)-catalyzed enantioselective hydrogenation
Wu, Hai-Chen,Hamid, Shafida Abd,Yu, Jin-Quan,Spencer, Jonathan B.
supporting information; experimental part, p. 9604 - 9605 (2011/03/19)
(Chemical Equation Presented) Reducing the electron density of ligands switches the regioselectivity of Rh(I)-catalyzed hydrometalation. A reversal of the sense of chiral induction was also observed when chiral ligands are electronically tuned in the same
Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C
Ousmer,Braun,Bavoux,Perrin,Ciufolini
, p. 7534 - 7538 (2007/10/03)
A solution to the long-standing problem presented by the oxidative cyclization of a phenolic 3-arylpropionamide to a spirolactam has been developed in this laboratory via oxazoline chemistry. This research was motivated by our interest in some novel tricyclic azaspirane natural products formally derived from tyrosine, such as FR901483 and TAN1251C. In this paper, we disclose full details of the total synthesis of these substances.
