Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 8
815
Views
2
CrossRef citations to date
0
Altmetric
Original Articles

Improved Enantioselective Synthesis of Protected (3S,4S)-4-Amino-3,5-dihydroxypentanoic Acid (ADPA)

, &
Pages 1099-1105 | Received 12 Mar 2009, Published online: 12 Mar 2010

REFERENCES

  • Gante , J. Peptidomimetics-tailored enzyme inhibitors . Angew Chem., Int. Ed. Engl. 1994 , 33 , 1699 – 1720 .
  • Umezawa , H. ; Aoyagi , T. ; Morishima , H. ; Matauzaki , H. ; Hamada , M. ; Takeuchi , T. Pepstatin, a new pepsin inhibitors produced by actinomycetes . J. Antibiot. 1970 , 23 , 259 – 260 .
  • Oh , D. ; Strangman , W. K. ; Kauffman , C. A. ; Jensen , P. R. ; Fenical , W. Thalassosiramides A and B, immunosuppressive peptides from the marine bacterium. Thalassospira sp. Org. Lett. 2007, 9, 1525–1528.
  • Hoffman , R. V. ; Tao , J. An improved enantiospecific synthesis of statine and statine analogs via 4-(N,N-dibenzylamino)-3-keto esters . J. Org. Chem. 1997 , 62 , 2292 – 2297 .
  • Hulme , A. N. ; Curley , K. S. Approaches to the synthesis of (2R,3S)-2-hydroxymethylpyrrolidin-3-ol (CYB-3) and its C(3) epimer: A cautionary tale . J. Chem. Soc., Perkin Trans. 1 2002 , 1 , 1083 – 1091 .
  • Brooks , D. W. ; Lu , D. L. ; Masamune , S. C-Acylation under virtually neutral conditions . Angew. Chem., Int. Ed. Engl. 1979 , 18 , 72 – 74 .
  • The methyl ester of 10a was converted to tert-butyl ester,  = −4.4 (c = 1.0, CDCl3), lit.  = −3.8 (c = 1.0, CDCl3). See Andres , J. M. ; Pedrosa , R. ; Pérez , A. ; Pérez-Encabo , A. Diastereoselective synthesis of enantiopure γ-amino-β-hydroxy acids by Reformatsky reaction of chiral α-dibenzylamino aldehydes . Tetrahedron 2001 , 57 , 8521 – 8530 .
  • Amiard , G. ; Heymes , R. ; Velluz , L. N,N-Dibenzylamino acids. Fr. Patent 66245 19560605 , 1956 .
  • Chandrasekhar , S. ; Reddy , C. R. ; Rao , R. J. Facile and selective cleavage of allyl ethers, amines, and esters using polymethylhydrosiloxane-ZnCl2/Pd(PPh3)4 . Tetrahedron 2001 , 57 , 3435 – 3438 .

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.