Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 5
329
Views
17
CrossRef citations to date
0
Altmetric
Original Articles

Stereoselective Synthesis of (+)-Nephrosteranic Acid by Ring-Closing Metathesis and Its Biological Evaluation

, , &
Pages 686-696 | Received 17 Jan 2009, Published online: 04 Feb 2010

REFERENCES

  • Jacobi , P. A. ; Herradura , P. Enantioselective synthesis of (+) and (−)-phaseolinic acid . Tetrahedron Lett. 1996 , 37 , 8297 – 8300 .
  • (a) Maier , M. S. ; Marimon , D. I. G. ; Stortz , C. A. ; Adler , M. T. A revised structure for (−)-dihydropertusaric acid, a γ-butyrolactone acid from the lichen Punctelia microsticta . J. Nat. Prod. 1999 , 62 , 1565 – 1567 ; (b) Lee , S. C. ; Brown , G. D. Tribenzylbutyrolactones and dibenzyldiphenyl-4,5,6,7-tetrahydrobenzofuranones from Kyrtuthrix maculans . J. Nat. Prod. 1998 , 61 , 29 – 33 .
  • (a) Loh , T. P. ; Lye , P. L. Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: A short synthesis of (−)-roccellaric acid . Tetrahedron Lett. 2001 , 41 , 561 – 563 ; (b) Mandal , P. K. ; Roy , S. C. Total synthesis of (±)-dihydroprotolichesterinic acid and formal synthesis of (±)-roccellaric acid by radical cyclisation of an epoxide using a transition-metal radical source . Tetrahedron 1999 , 55 , 11395 – 11398 ; (c) Lertvorachon , J. ; Meepowpan , P. ; Thebtaranonth , Y. An aldol-bislactonization route to α-methylene bis-γ-butyrolactones . Tetrahedron 1998 , 54 , 14341 – 14348 ; (d) Mandal , P. K. ; Maiti , G. ; Roy , S. C. Stereoselective synthesis of polysubstituted tetrahydrofurans by radical cyclization of epoxides using a transition-metal radical source: Application to the total synthesis of (±)-methylenolactocin and (±)-protolichesteranic acid . J. Org. Chem. 1998 , 63 , 2829 – 2834 .
  • (a) Masaki , Y. ; Arasaki , H. ; Itoh , A. Enantiodivergent synthesis of both enantiomeric forms of substituted paraconic acids starting from mannitol as a chiral pool . Tetrahedron Lett. 1999 , 40 , 4829 – 4832 ; (b) Mulzer , J. ; Salimi , N. ; Hartl , H. First asymmetric synthesis of (+) and (−)-roccellaric acid and dihydroprotolichesterinic acid . Tetrahedron: Asymmetry 1993 , 4 , 457 – 471 .
  • (a) Bella , V. ; Margarita , V. ; Orlando , C. ; Orsini , M. ; Parlanti , L. ; Piancatelli , G. α-Cyano-γ-lactones by photoinduced electron-transfer-catalyzed oxidation of α-hydroxyalkylsilanes in the prescence of α-cyano acrylates . Tetrahedron Lett. 2000 , 41 , 561 – 565 ; (b) Sibi , M. P. ; Ji , J. Regio-and stereocontrolled conjugate radical addition to a desymmetrized fumarate derivative: An efficient synthesis of (−)-nephrosteranic acid and (−)-roccellaric acid . Angew. Chem., Int. Ed. Engl. 1997 , 36 , 274 – 276 ; (c) Murta , M. M. ; de Azevedo , M. B. M. ; Greene , A. E. Synthesis and absolute stereochemistry of (−)-protolichesterinic acid, antitumor antibiotic lactone from Cetraria islandica . J. Org. Chem. 1993 , 58 , 7537 – 7541 .
  • (a) Chandrasekharam , M. ; Liu , R. S. An aldol-bislactonization route to α-methylene bis-γ-butyrolactones: Synthesis of natural α-methylene butyrolactones via tungsten-π-allyl complexes: Total synthesis of (−)-methylenolactocin . J. Org. Chem. 1998 , 63 , 9122 – 9124 ; (b) Vaupel , A. ; Knochel , P. Stereoselective synthesis of heterocyclic zinc reagents via a nickel-catalysed radical cyclization . J. Org. Chem. 1996 , 61 , 5743 – 5753 .
  • Barros , M. T. ; Maycock , C. D. ; Venturia , M. R. Aldol reactions of diaxanes derived from tartaric acid: A total synthesis of nephrosteranic acid . Org. Lett. 2003 , 5 , 4097 – 4099 .
  • (a) Narender , P. ; Gangadasu , B. ; Ramesh , C. ; China Raju , B. ; Rao , V. J. Facile and selective synthesis of chloromethylpyridines and chloropyridines using diphosgene/triphosgene . Synth. Commun. 2004 , 34 , 1097 – 1103 ; (b) Gangadasu , B. ; Narender , P. ; Bharath Kumar , S. ; Ravinder , M. ; Ananda Rao , B. ; Ramesh , C. ; China Raju , B. ; Rao , V. J. Facile and selective synthesis of chloronicotinaldehydes by the Vilsmeier reaction . Tetrahedron 2006 , 62 , 8398 – 8403 ; (c) Narender , P. ; Srinivas , U. ; Gangadasu , B. ; Biswas , S. ; Rao , V. J. Anti-malarial activity of Baylis–Hillman adducts from substituted 2-chloronicotinaldehydes . Bioorg. Med. Chem. Lett. 2005 , 15 , 5378 – 5381 ; (d) Srinivas , K. ; Srinivas , U. ; Bhanuprakash , K. ; Harakishore , K. ; Murthy , U. S. N. ; Rao , V. J. Synthesis and antibacterial activity of various substituted s-triazines . Eur. J. Med. Chem. 2006 , 41 , 1240 – 1246 ; (e) Srinivasa Rao , M. ; Murty , U. S. N. ; Gangadasu , B. ; China Raju , B. ; Ramesh , C. ; Bharat Kumar , S. ; Rao , V. J. Larvicidal efficacy of neonicotinoid classes of compounds on Culexquinquefasciatus . J. Entomol. 2008 , 5 , 45 – 50 .
  • Hon , Y. S. ; Lu , L. ; Li , S. Y. The reaction of ozonides from mono-substituted alkenes with stabilized phosphorus ylides . J. Chem. Soc., Chem. Commun. 1990 , 1627 – 1628 .
  • Park , S. U. ; Chung , S. K. ; Newcomb , M. Evidence supporting two-electron nucleophilic displacement in reactions of unhindered alkyl bromides and iodides with boron and aluminum hydride reducing agents . J. Org. Chem. 1987 , 52 , 3275 – 3278 .
  • Gao , Y. ; Hanson , R. M. ; Klunder , J. M. ; Ko , Y. S. ; Masamune , H. ; Sharpless , B. K. Catalytic asymmetric epoxidation and kinetic resolution: Modified procedures including in situ derivatization . J. Am. Chem. Soc. 1987 , 109 , 5765 – 5780 .
  • Liu , Z. ; Lan , J. ; Li , Y. Facile one-pot transformation of 2,3-epoxy alcohols into allylic alcohols: First total synthesis of (−)-4-O-(6′-hydroxy-7′(9′)-dehyro-6′,7′-dihydrogeranyl)coniferol . Tetrahedron: Asymmetry 1998 , 9 , 3755 – 3762 .
  • Ghosh , K. A. ; Liu , C. A stereoselective synthesis of (−)-tetrahydrolipstatin . Chem. Commun. 1999 , 1743 – 1744 .
  • (a) Grubbs , R. H. ; Miller , S. J. ; Fu , G. C. Ring-closing metathesis and related processes in organic synthesis . Acc. Chem. Res. 1995 , 28 , 446 – 452 ; (b) Schuster , M. ; Blechert , S. Olefin metathesis in organic chemistry . Angew. Chem., Int. Ed. Engl. 1997 , 36 , 2036 – 2056 ; (c) Bassetti , M. ; Annibale , A. D. ; Fanfoni , A. ; Minissi , F. Synthesis of α,β-unsaturated 4,5-disubstituted γ-lactones via ring-closing metathesis catalyzed by the first-generation Grubb's catalyst . Org Lett. 2005 , 7 , 1805 – 1808 .
  • Harding , E. K. ; Clement , A. B. ; Moreno , L. ; Katalinic , J. P. Synthesis of some polyfunctionalized bicyclo[3.3.1]nonane-2,9-diones and bicyclo[4.3.1]decane-2,10-diones . J. Org. Chem. 1981 , 46 , 940 – 948 .
  • Schollkopf , U. ; Paust , J. ; Patsch , M. R. Org. Synth., Coll. Vol. V , 1973 , 859 .
  • Marshall , J. A. ; Brady , S. F. The total synthesis of (±)-hinesol . J. Org. Chem. 1970 , 35 , 4068 – 4077 .
  • House , H. O. ; Thompson , H. W. The chemistry of carbanions IV: The stereochemistry of conjugated Grignard addition . J. Org. Chem. 1963 , 28 , 360 – 365 .
  • Seki , M. ; Shimizu , T. ; Matsumoto , K. Stereoselective synthesis of β-benzyl-α-alkyl-β-amino acids from L-aspartic acid . J. Org. Chem. 2000 , 65 , 1298 – 1304 .
  • Mulzer , J. ; Kattner , L. ; Strecker , R. A. ; Schroder , C. ; Buschmann , J. ; Lehmann , C. ; Luger , P. ; Felkin , A. Highly selective Hiyama additions of chiral allylic bromides to aldehydes: Application to the first synthesis of nephromopsinic acid and its enantiomer. J. Am. Chem. Soc. 1991, 113, 4218–4229.
  • (a) National Committee for Clinical Laboratory Standard . Reference Method for Broth Dilution Antifungal Susceptibility ; National Committee for Clinical Laboratory Standards : Wayne , PA , 1997 ; (b) National Committee for Clinical Laboratory Standard . Reference Method for Broth Dilution Antifungal Susceptibility ; National Committee for Clinical Laboratory Standard : Wayne , PA , 1998 .
  • Mosmann , T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays . J. Immunol. Methods 1983 , 65 , 55 .

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.