Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 22
475
Views
3
CrossRef citations to date
0
Altmetric
Original Articles

Concise Stereoselective Total Synthesis of (4R, 6R)-Lactone Moiety Analog of Mevinoline and Compactin

, , , &
Pages 2980-2984 | Received 18 Jul 2012, Published online: 08 Aug 2013

REFERENCES

  • Alberts , A. W. ; Chen , J. ; Kuron , G. ; Hunt , V. ; Huff , J. ; Hoffman , C. ; Rothrock , J. ; Lopez , M. ; Joshua , H. ; Harris , E. ; Patchett , A. ; Monaghan , R. ; Currie , S. ; Stapley , E. ; Albersshonberg , G. ; Hensens , O. ; Hirshfield , J. ; Hoogsteen , K. ; Liesch , J. Mevinolin: A highly potent competitive inhibitor of hydroxymethylglutaryl-coenzyme A reductase and a cholesterol-lowering agent . J. Proc. Natl. Acad. Sci. USA 1980 , 77 , 3957 – 3961 .
  • Endo , A. ; Kuroda , M. ; Tsujita , Y. J. ML-236-A, ML236-B, ML-236-C, new inhibitors of cholesterogenesis produced by Penicillium citrinium . J. Antibiot. 1976, 29, 1346–1348.
  • Kaneko , I. ; Hazama-Shimada , Y. ; Endo , A. Therapeutic response to Lovastatin (mevilonin) in nonfamilial hypercholesterolemia . J. Am. Med. Assoc. 1986 , 256 , 2829 – 2834 .
  • Kaneko , I. ; Hazama-Shimada , Y. ; Endo , A. Inhibitory effects on lipid metabolism in cultured cells of ML-236-B, a potent inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme-A reductase . Eur. J. Biochem. 1978 , 87 , 313 – 321 .
  • Jendralla , H. ; Baader , E. ; Bartmann , W. ; Beck , G. ; Bergmann , A. ; Granzer , E. ; Kerekjarto , B. V. ; Kesseler , K. ; Krause , R. ; Schubert , W. ; Wess , G. Synthesis and biological activity of new HMG-CoA reductase inhibitors: Derivatives of 7-(1H-pyrrol-3-yl)-substituted-3,5-dihydroxyhept-6(E)-enoic-(heptanoic) acids . J. Med. Chem. 1990 , 33 , 61 – 70 .
  • Hoffman , W. F. ; Alberts , A. W. ; Anderson , P. S. ; Chen , J. S. ; Smith , R. L. ; Willard , A. K. 3-Hydroxy, 3-methylglutaryl-coenzyme A reductase inhibitors: Side-chain ester dervatives of mevinolin . J. Med. Chem. 1986 , 29 , 849 – 852 .
  • Lynch , J. E. ; Volante , R. P. ; Wattley , R. V. ; Shinkai , I. Synthesis of an HMG-CoA reductase inhibitor: Diastereoselective aldol approach . Tetrarahedron Lett. 1987 , 28 , 1385 – 1387 .
  • Heathcock , C. H. ; Davis , B. R. ; Hadly , C. R. Synthesis and biological evalution of monocyclic, fully functional analogue of compactin . J. Med. Chem. 1989 , 32 , 197 – 202 .
  • Srikanth Reddy , T. ; Kumar Reddy , D. ; Narasimhulu , M. ; Ramesh , D. ; Venkateswarlu , Y. Total synthesis of mevinic acid analog . Helv. Chem. Acta. 2010 , 93 , 2158 – 2163 , and references cited therein.
  • Kumar , P. ; Pandey , M. ; Gupta , P. ; Dhavale , D. D. An organocatalytic route to the synthesis of lactone moiety of compactin and mevinolin . Tetrahedron Lett. 2010 , 51 , 5838 – 5839 .
  • Rao , C. B. ; Rao , D. C. ; Babu , D. C. ; Venkateswarlu , Y. Retro-Claisen condensation with Fe (III) as catalyst under solvent-free conditions . Eur. J. Org. Chem. 2010 , 15 , 2855 – 2859 .
  • (a) Balaji , B. S. ; Chanda , B. M. Simple and high-yielding syntheses of β-keto esters catalysed by zeolites . Tetrahedron 1998 , 54 , 13237 – 13252 ; (b) Jeyakumar , K. ; Dillip Kumar , C. Molybdenum(VI) dichloride dioxide–catalyzed synthesis of β-keto esters by C-H insertion of ethyl diazoacetate into aldehydes . Synthesis 2008 , 11 , 1685 – 1687 ; (c) Yadav , J. S. ; Subba Reddy , B. V. ; Eeshwaraiah , B. ; Reddy , P. N. Niobium(V) chloride–catalyzed C-H insertion reactions of α-diazoesters: Synthesis of β-keto esters . Tetrahedron 2005 , 4 , 875 – 878 ; (d) Christopher , R. H. ; Roskamp , E. J. A selective method for the direct conversion of aldehydes into β-keto esters with ethyl diazoacetate catalyzed by tin(II) chloride . J. Org. Chem. 1989 , 54 , 3258 – 3260 ; (e) Matthew , E. D. ; Md. Monzur , M. ; Courtney , L. B. ; Islam , M. S. ; Ahmad , M. S. ; Mary-Rose , A. ; Bryan , B. ; Hossain , M. M. Acid-catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: An investigation on the synthesis of 3-hydroxy-2 arylacrylic acid ethyl esters . J. Org. Chem. 2004 , 69 , 7599 – 7608 ; (f) Rajesh , K. P. ; Anis , D. N. ; Kumar , P. Synthesis of β‐keto esters promoted by yttria‐zirconia-based lewis acid catalyst . Synth. Commun. 2004 , 34 , 1117 – 1124 .
  • Kumar Reddy , D. ; Shekhar , V. ; Srikanth Reddy , T. ; Purushotham Reddy , S. ; Venkateswarlu , Y. Stereoselctive first total synthesis of (R)-rugulactone . Tetrahedron: Asymmetry 2009 , 20 , 2315 – 2319 .
  • Dubost , C. ; Markó , I. E. ; Ryckmans , T. A concise total synthesis of the lichen macrolide (+)-aspicilin . Org. Lett. 2006 , 8 , 5137 – 5140 .
  • Evans , D. A. ; Rieger , D. L. ; Gage , J. R. 13C NMR correlations in 1,3-diol acetonides: Implications for the stereochemic assignment of propionate-derived polyols . Tetrahedron Lett. 1990 , 31 , 7099 – 7100 .
  • Sudhakar , K. ; Srinivas , C. ; Yadav , J. S. ; Sabitha , G. Stereoselective synthesis of a Mevinic acid analogue . Synthesis 2007 , 5 , 705 – 708 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.