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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 16
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Original Articles

Stereoselective Synthesis of Two New Trihydroxylated Pyrrolidines Using a Meyer–Schuster Rearrangement

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Pages 2435-2445 | Received 31 May 2010, Published online: 14 Jun 2011

REFERENCES

  • (a) Asano , N. In Modern Alkaloids: Structure, Isolation, Synthesis, and Biology ; E. Fattorusso , O. Taglialatela-Scafati (Eds.); Wiley-VCH : Weinheim , 2008 ; pp. 11 – 138 ; (b) Asano , N. In Glycoscience: Chemistry and Chemical Biology ; B. O. Fraser-Reid , K. Tatsuta , J. Thiem (Eds.); Springer : Berlin , 2008 ; pp. 1887 – 1911 .
  • For a recent review on the Meyer–Schuster rearrangement, see Engel , D. A. ; Dudley , G. B. The Meyer–Schuster rearrangement for the synthesis of α,β-unsaturated carbonyl compounds . Org. Biom. Chem. 2009 , 7 , 4149 – 4158 .
  • (a) Chamberlin , A. R. ; Chung , J. Y. Synthesis of optically active pyrrolizidinediols: (+)-Heliotridine . J. Am. Chem. Soc. 1983 , 105 , 3653 – 3656 ; (b) Choi , J.-K. ; Hart , D. J. Free radical cyclizations in alkaloid synthesis: (+)-Heliotridine and (+)-hastanecine . Tetrahedron 1985 , 41 , 3959 – 3971 .
  • (a) Zhou , X. ; Huang , P.-Q. A versatile approach to protected (4S,5R)-4-hydroxy-5-(α-hydroxyalkyl)-2-pyrrolidinones . Synlett 2006 , 1235 – 1239 ; (b) Zhou , X. ; Zhang , P.-Y. ; Ye , J.-L. ; Huang , P.-Q. A versatile approach to (4S,5R)-4-benzyloxy-5-(α-hydroxyalkyl)-2-pyrrolidinones: Experimental evidence to the computational predictions . Compt. Rend. Chim. 2008 , 11 , 5 – 18 .
  • (a) Dugisaki , C. H. ; Carroll , P. J. ; Correia , R. D. Differential oxidation of endocyclic enecarbamates: Synthesis of cyclic β-hydroxy-α-amino acids . Tetrahedron Lett. 1998 , 39 , 3413 – 3416 ; (b) Sunose , M. ; Anderson , K. M. ; Orpen , A. G. ; Gallagher , T. ; Macdonald , S. J. F. Synthesis of 3-hydroxy and 3-amino 2-substituted N-heterocycles via enamine oxidation and aziridination . Tetrahedron Lett. 1998 , 39 , 8885 – 8888 .
  • Huang has prepared related compounds from the oxidation of similar enamides with oxone/MeOH or mCPBA/MeOH. See Ref. 4b ; Zhou , X. ; Liu , W.-J. ; Ye , J.-L. ; Huang , P.-Q. Complementary stereocontrolled approaches to 2-pyrrolidinones bearing a vicinal amino diol subunit with three continuous chiral centers: A formal asymmetric synthesis of (−)-detoxinine . J. Org. Chem. 2007 , 72 , 8904 – 8909 .
  • Morgan , I. R. ; Yazici , A. ; Pyne , S. G. Metal-catalysed cycloisomerization reactions of cis-4-hydroxy-5-alkynylpyrrolidinones and cis-5-hydroxy-6-alkynylpiperidinones: Synthesis of furo[3,2-b]pyrroles and furo[3,2-b]pyridines . Tetrahedron 2008 , 64 , 1409 – 1419 .
  • Winqvist , A. ; Stromberg , R. Stereoselectivity in the synthesis of 3′-deoxy-3′-C-(hydroxymethyl)uridines by hydroboration and conversion into a building block for various 3′-deoxy-3′-C-(methylene)uridine analogues . Eur. J. Org. Chem. 2001 , 4305 – 4311 .

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