Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
150
Views
4
CrossRef citations to date
0
Altmetric
Original Articles

First Asymmetric Total Synthesis of (R,E)-1-[4-(3-Hydroxyprop-1-enyl)phenoxyl]-3-methylbutane-2,3-diol

, , &
Pages 993-998 | Received 03 Dec 2009, Published online: 03 Mar 2011

REFERENCES

  • Masuda , T. ; Inazumi , A. ; Yamada , Y. ; Padolina , W. G. ; Kikuzaki , H. ; Nakatani , N. Antimicrobial phenylpropanoids from Piper sarmentosum . Phytochemistry 1991 , 30 , 3227 – 3228 .
  • Zaeoung , S. ; Plubrukarn , A. ; Keawpradub , N. Cytotoxic and free radical scavenging activities of Zingiberaceous rhizomes . Songklanakarin J. Sci. Technol. 2005 , 27 , 799 – 812 .
  • Sakagami , H. ; Kawazoe , Y. ; Komatsu , N. ; Simpson , A. ; Nonoyama , M. ; Konno , K. ; Yoshida , T. ; Kuroiwa , Y. ; Tanuma , S.-I. Antitumor, antiviral, and immunopotentiating activities of pine cone extracts: Potential medicinal efficacy of natural and synthetic lignin-related materials (review) . Anticancer Res. 1991 , 11 , 881 – 888 .
  • Compton , D. L. ; Laszlo , J. A. 1,3-Diferuloyl-sn-glycerol from the biocatalytic transesterification of ethyl 4-hydroxy-3-methoxy cinnamic acid (ethyl ferulate) and soybean oil . Biotechnol. Lett. 2009 , 31 , 889 – 896 .
  • Chen , J.-J. ; Chen , P.-H. ; Liao , C.-H. ; Huang , S.-Y. ; Chen , I.-S. New phenylpropenoids, bis(1-phenylethyl)phenols, bisquinolinone alkaloid, and anti-inflammatory constituents from Zanthoxylum integrifoliolum . J. Nat. Prod. 2007 , 70 , 1444 – 1448 .
  • Chang , C. E. ; Hartley , T. G. Rutaceae in Flora of Taiwan, , 2nd ed. ; Editorial Committee of the Flora of Taiwan : Taipei , Taiwan , 1993 ; vol. 3 , pp. 510 – 544 .
  • Ko , F. N. ; Hsiao , G. ; Chen , I. S. ; Wu , S. J. ; Teng , C. M. Inhibition of collagen-induced platelet aggregation and adhesion by a pseudocyanide derivative of avicine isolated from Zanthoxylum integrifoliolum MRRR . Biochem. Pharmacol. 1993 , 46 , 1165 – 1173 .
  • Ishii , H. ; Chen , I. S. ; Akaike , M. ; Ishikawa , T. ; Lu , S. T. Studies on the chemical constituents of rutaceous plants, XLIV: The chemical constituents of Zanthoxylum integrifoliolum (Merr.) Merr. (Fagara integrifoliola Merr.), 1: The chemical constituents of the root wood . Yakugaku Zasshi. 1982 , 102 , 182 .
  • Jen , C. M. ; Tsai , I. L. ; Horng , D. J. ; Chen , I. S. Isolation and structure determination of two new compounds from Zanthoxylum integrifoliolum . J. Nat. Prod. 1993 , 56 , 2019 .
  • (a) Chen , I. S. ; Chen , T. L. ; Lin , W. Y. ; Tsai , I. L. Isobutylamides from the fruit of Zanthoxylum integrifoliolum . Phytochemistry 1999, 52, 357; (b) Chen , I. S. ; Chen , T. L. ; Chang , Y. L. ; Teng , C. M. ; Lin , W. Y. Chemical constituents and biological activities of the fruit of Zanthoxylum integrifoliolum. J. Nat. Prod. 1999, 62, 833.
  • (a) Kolb , H. C. ; Van Niewenhze , M. S. ; Sharpless , K. B. Catalytic asymmetric dihydroxylation . Chem. Rev. 1994 , 94 , 2483 ; (b) Banwell , M. G. ; Chand , S. ; Savage , G. P. An enantioselective total synthesis of the stilbenolignan (−)-aiphanol and the determination of its absolute stereochemistry . Tetrahedron: Asymmetry 2005 , 16 , 1645 .
  • (a) Becker , H. ; Ho , P. T. ; Kolb , H. C. ; Loren , S. ; Norrby , P. O. ; Sharpless , K. B. Comparing two models for the selectivity in the asymmetric dihydroxylation reaction (AD) . Tetrahedron Lett. 1994 , 35 , 7315 ; (b) Kolb , H. C. ; Andersson , P. G. ; Sharpless , K. B. Toward an understanding of the high enantioselectivity in the osmium-catalyzed asymmetric dihydroxylation (AD), 1: Kinetics . J. Am. Chem. Soc. 1994 , 116 , 1278 ; (c) Sauret , S. ; Cuer , A. ; Gourcy , J. G. ; Jeminet , G. Chiral 2- and 8-functionalised 1,7-dioxaspiro[5.5]undecanes via asymmetric dihydroxylation . Tetrahedron: Asymmetry 1995 , 6 , 1995 .
  • Yadav , J. S. ; Raju , A. K. ; Rao , P. P. ; Rajaiah , G. Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone . Tetrahedron: Asymmetry 2005 , 16 , 3283 .
  • Daniewski , A. R. ; Wojceichowska , W. Synthesis of the corticoid side chain . J. Org. Chem. 1982 , 47 , 2993 .

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.