Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 34, 2004 - Issue 13
388
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of (−)‐Mintlactone via Intramolecular Wittig–Horner Reaction

, , &
Pages 2323-2329 | Received 17 Feb 2004, Published online: 30 Mar 2009

References

  • Muraki , S. 1968 . Abstract of Papers 12th Symposium on the Chemistry of Terpenes Essential Oil and Aromatics . 1968 , Shizuoka, Japan. pp. 13
  • Fujita , S. and Fujita , Y. 1972 . Isolation of (−)‐minlactone from M. pulegium L . Nippon Nageikagaku Kaishi , 46 : 303 – 307 .
  • Sakata , I. and Hashizume , T. 1973 . Constituents of Japanese peppermint oil. V. Isolation and identification of 2,3‐dimethyl‐4‐hydroxy‐2‐nonenoic acid from lactone from Shubi . Agric. Biol. Chem. , 37 : 2441 – 2442 .
  • Cory , R. M. , Ritchie , B. M. and Shrier , A. M. 1990 . A versatile synthesis of butenolides: total synthesis of (+/−)‐mintlactone . Tetrahedron Lett. , 31 : 6789 – 6792 .
  • Näf , R. and Velluz , A. 1998 . Phenols and lactones in halo‐mitcham peppermint oil Menthax piperita L . Flavor Fragrance J. , 13 : 203 – 208 .
  • Takahashi , K. , Someya , T. , Muraki , S. and Yoshida , T. 1980 . Chemical composition of fragrant maetirals. Part IV. A new keto‐alcohol (−) mintlactone, (+)‐isomintlactone and minor components in peppermint oil . Agric. Biol. Chem. , 44 : 1535 – 1543 .
  • Foote , C. S. , Wuesthoff , M. T. , Wexler , S. , Schenck , G. O. and Schule‐Elte , K.‐H. 1967 . Photosensitized oxygenation of alkyl‐substituted furans . Tetrahedron , 23 : 2583 – 2599 .
  • Hirsch , J. A. and Estmann , R. H. 1967 . Hydrolysis of α,α‐dimethoxydihyromenthofuran . J. Org. Chem. , 32 : 2915 – 2916 .
  • Shishido , K. , Irie , O. and Shibuya , M. 1992 . An efficient total synthesis of (−)‐mintlactone and (+)‐isomintlactone . Tetrahedron Lett. , 33 : 4589 – 4592 .
  • Chavan , S. P. , Zubaidha , P. K. and Dhondge , V. D. 1993 . A short and efficient total synthesis of (−) mintlactone and (+) iso‐mintlactone . Tetrahedron , 49 : 6429 – 6436 .
  • Ferraz , H. M.C. , Gragini , M. V.A. , Ribeiro , C. M.R. , Brocksom , U. and Brocksom , T. J. 2000 . A short route to (−)‐mintlactone by thallium (III)‐mediated cyclisation of (−)‐isopulegol . J. Org. Chem. , 65 : 2606 – 2607 .
  • Tadwalkar , V. R. and Rao , A. S. 1971 . Synthesis of p‐menthenolides . Ind. J. Chem. , 9 : 1416 – 1417 .
  • Fujita , T. , Watanabe , S. , Mihura , K. , Itoh , K. and Sugahara , K. 1985 . A convenient preparative method for mintlactone and isomintlactone . J. Chem. Tech. Biotech. Chem. Tech. , 35 A : 57 – 62 .
  • Lohray , B. B. , Nandana , E. and Bhushan , V. 1997 . Reversal of facial selectivity in the kinetic resolution of olefin via asymmetric dihydroxylation (AD) reaction: synthesis of optically active (−)‐mintlactone and (+)‐isomintlactone by AD reaction from intrinsically disfavored diastereoface of alkenes . Ind. J. Chem. Sect. B , 36 : 226 – 231 .
  • Tanyeli , C. , Cahskan , Z. and Demir , A. S. 1997 . A facile synthesis of (+/−)‐mintlactone . Synth. Commun. , 27 : 3471 – 3476 .
  • Carda , M. and Macro , J. A. 1992 . Total synthesis of the monoterpenes (−)‐mintlactone and (+)‐isomintlactone . Tetrahedron , 40 : 9789 – 9800 .
  • Shimizu , M. , Kamikubo , T. and Ogasawara , K. 1998 . An enantio‐ and diastereocontrolled route to mintlactone using a chiral cyclohexadienone equivalent . Synlett , : 655 – 657 .
  • Ferraz , H. M.C. , Luiz , S. L. and Grazini , M. V.A. 2002 . Synthesis of mintlactone and isomintlactone . Synthesis , : 2155 – 2164 .
  • Kumar , P. , Dinesh , C. U. and Pandey , B. 1994 . An efficient synthesis of quinolones using N‐phenyl(triphenylphosphoranylidene) ethenimine . Tetrahedron Lett. , 35 : 9229 – 9232 .
  • Kumar , P. , Rao , A. T. and Pandey , B. 1994 . Chemoselective reduction of vinylogous thioesters of thiochromones . Synth. Commun. , 24 : 3297 – 3306 .
  • Kumar , P. and Saravanan , K. 1998 . Facile synthesis of unsaturated lactones via intramolecular Wittig reaction . Tetrahedron , 54 : 2161 – 2168 .
  • Kumar , P. and Bodas , M. S. 2000 . A novel synthesis of 4H‐chromen‐4‐ones via intramolecular Wittig reaction . Org. Lett. , 2 : 3821 – 3823 .
  • Kumar , P. and Bodas , M. S. 2001 . A novel synthesis of 4H‐1‐benzothiopyran‐4‐ones using (trimethylsilyl)methylenetriphenylphosphorane . Tetrahedron , 57 : 9755 – 9758 .
  • Luche , J.‐L. 1978 . Lanthanides in organic chemistry. 1. Selective 1,2 reduction of conjugated ketones . J. Am. Chem. Soc. , 100 : 2226 – 2227 .
  • Luche , J.‐L. , Rodriguenz‐Hahn , L. and Crabbe , P. 1978 . Reduction of natural enones in the presence of cerium trichloride . Chem. Commun. , : 601 – 602 .
  • Sayo , N. and Matsumoto , T. Processes for the Preparation of 1‐Menthol via Successive Enantioselective Hydrogenation Catalyzed by Transition Metal Complexes . Eur. Pat. 401,180 . 2001 .
  • Ohkuma , T. , Ikehira , H. , Ikariya , T. and Noyori , R. 1997 . Asymmetric hydrogenation of cyclic α,β‐unsaturated ketones to chiral allylic alcohols . Synlett. , : 467 – 468 .
  • Borszeky , K. , Mallat , T. and Baiker , A. 1997 . Enantioselective hydrogenation of α,β‐unsaturated acids. Substrate‐modifier interaction over cinchonidine modified Pd/Al2O3 . Tetrahedron: Asymmetry , 8 : 3745 – 3753 .
  • Grison , C. , Comoy , C. and Coutrot , P. 2001 . Towards synthesis of a peptidophosphoryl antibiotic, alaphosphaline. Synthesis and characterization of a modified peptide incorporating a C‐terminal phosphorus containing group . Actual. Chimique , 10 : 38 – 48 .

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.