Diversity-oriented synthesis of enantiopure N-protected β,β-dialkylserines

2004 ◽  
Vol 82 (2) ◽  
pp. 318-324 ◽  
Author(s):  
James E Dettwiler ◽  
William D Lubell
Keyword(s):  
Amino Acid ◽  
Methyl Ester ◽  
Grignard Reagent ◽  
Primary Alcohol ◽  
Sodium Chlorite ◽  
Ring Closing Metathesis ◽  
Diversity Oriented Synthesis ◽  
Enantiomerically Pure ◽  
Catalysed Oxidation

A series of enantiomerically pure N-Boc-protected β,β-dialkylserines was synthesized by addition of the appropriate Grignard reagent to N-(Boc)serine methyl ester, followed by TEMPO-catalysed oxidation of the primary alcohol with sodium chlorite and sodium hypochlorite.Key words: amino acid, serine, β,β-dialkylserines, ring-closing metathesis.

Alkene Metathesis: Synthesis of Panaxytriol (Lee), Isofagomine (Imahori and Takahata), Elatol (Stoltz), 5-F2t -Isoprostane (Snapper), and Ottelione B (Clive)

2011 ◽  
Author(s):  
Douglass Taber
Keyword(s):  
Grignard Reagent ◽  
Conjugate Addition ◽  
Ring Closing Metathesis ◽  
University Of Illinois ◽  
Enantiomerically Pure ◽  
University Of Alberta ◽  
Cross Metathesis ◽  
Grubbs Catalysts ◽  
The University ◽  
First And Second Generation

Alkene metathesis has been used to prepare more and more challenging natural products. The first and second generation Grubbs catalysts 1 and 2 and the Hoveyda catalyst 3 are the most widely used. Daesung Lee of the University of Illinois at Chicago designed (Organic Lett. 2008, 10, 257) a clever chain-walking cross metathesis, combining 4 and 5 to make 6. The diyne 3 was carried on (3R, 9R, 10R )-Panaxytriol 7. Tatsushi Imahori and Hiroki Takahata of Tohoku Pharmaceutical University found (Tetrahedron Lett. 2008, 49, 265) that of the several derivatives investigated, the unprotected alcohol 8 cyclized most efficiently. Selective cleavage of the monosubstituted alkene followed by hydroboration delivered the alkaloid Isofagomine 10. Brian M. Stoltz of Caltech established (J. Am. Chem. Soc. 2008 , 130 , 810) the absolute configuration of the halogenated chamigrene Elatol 14 using the enantioselective enolate allylation that he had previously devised. A key feature of this synthesis was the stereocontrolled preparation of the cis bromohydrin. Marc L. Snapper of Boston College opened (J. Org. Chem. 2008, 73, 3754) the strained cyclobutene 15 with ethylene to give the diene 16. Remarkably, cross metathesis with 17 delivered 18 with high regioselectivity, setting the stage for the preparation of the 5-F2t - Isoprostane 19. Derrick L. J. Clive of the University of Alberta assembled (J. Org. Chem. 2008, 73, 3078) Ottelione B 26 from the enantiomerically-pure aldehyde 20. Conjugate addition of the Grignard reagent 21 derived from chloroprene gave the kinetic product 22, that was equilibrated to the more stable 23. Addition of vinyl Grignard followed by selective ring-closing metathesis then led to 26.

Convenient Synthetic Route to an Enantiomerically Pure FMOC α-Amino Acid

2008 ◽  
Vol 73 (23) ◽  
pp. 9334-9339 ◽  
Author(s):  
Douglass F. Taber ◽  
James F. Berry ◽  
Timothy J. Martin
Keyword(s):  
Amino Acid ◽  
Synthetic Route ◽  
Enantiomerically Pure

scholarly journals Enantiomerically Pure [2.2]Paracyclophane-4-thiol: A Planar Chiral Sulfur-Based Building Block Readily Available by Resolution with an Amino Acid Chiral Auxiliary

2016 ◽  
Vol 81 (9) ◽  
pp. 3961-3966 ◽  
Author(s):  
Adrien Vincent ◽  
Damien Deschamps ◽  
Thomas Martzel ◽  
Jean-François Lohier ◽  
Christopher J. Richards ◽  
...  
Keyword(s):  
Amino Acid ◽  
Building Block ◽  
Chiral Auxiliary ◽  
Enantiomerically Pure
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