Synthesis of a designed sesquiterpenoid that forms useful composites with peptides and related oligomers

Tetrahedron Letters

Volumn 52, Issue 6, 2011, Pages 653-654

  Lawson, Kenneth V ^a   Rose, Tristan E ^a   Harran, Patrick G ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ISOPHTHALALDEHYDE; OLIGOMER; PEPTIDE; SESQUITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CRYSTALLIZATION;

EID: 79251597648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.083     Document Type: Article

References (16)

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2. Engaging structure 1 with synthetic WWY in a simple three step reaction sequence (see Ref. 1) leads to products such as 5, wherein the composite has restricted conformational mobility, increased stability and solubility and harbors both polar and hydrophobic domains.
3. S.G. Ouellet, A. Walji, and D.W.C. MacMillan Acc. Chem. Res. 40 2007 1327 and references therein
4. Reactions of scalemic 1 with enantiopure polyamides generate diastereoisomeric product mixtures which are difficult to separate. This unnecessarily complicates analysis/characterization.
5. D.M. Hobbs, P. Schubert, and H.-H. Tung Ind. Eng. Chem. Res. 36 1997 5302
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8. For 'SuperQuat' auxilaries see: S.D. Bull, S.G. Davies, S. Jones, M.E.C. Polywka, R.S. Prasad, and H.J. Sanganee Synlett 1998 519
9. J. Jacob, J.H. Espenson, J.H. Jensen, and M.S. Gordon Organometallics 17 1998 1835
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12. Readily prepared on >300 mmol scale according to: J. Bian, M. Van Wingerden, and J.M. Ready J. Am. Chem. Soc. 128 2006 7428
13. D.M. Pinkerton, M.G. Banwell, and A.C. Willis Aust. J. Chem. 62 2009 1639
14. Enantiomeric excess of 1 is determined via HPLC analysis of diastereoisomeric imidazolidines formed by reaction with (R,R)-N,N′- dimethyl-1,2-diphenyl ethylene diamine. Reaction with racemic 1 serves as a standard. See: P. Mangeney, A. Alexakis, and J.F. Normant Tetrahedron Lett. 29 1988 2677
15. D. Cuvinot, P. Mangeney, A. Alexakis, J.F. Normant, and J.P. Lellouche J. Org. Chem. 54 1989 2420
16. 3). This is signed opposite to previously synthesized 1, which was drawn incorrectly in our previous communication (Ref. 1).