- Stereoselective synthesis of (-)-N-Boc-AHPPA
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An efficient method has been developed for the stereoselective synthesis of N-Boc-AHPPA (7), a biologically important amino acid of non-proteinogenic origin.
- Veeresa
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- A practical route to enantiopure 3-hydroxy-pyrrolidines: application to a straightforward synthesis of (-)-bulgecinine
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A practical synthesis of enantiopure substituted 3-hydroxy-pyrrolidines is reported. In four steps, starting from commercially available amino acids as chiral educts, this method allows for an efficient preparation of a variety of 3-hydroxy-pyrrolidines, as well as 3-hydroxy-piperidines and azepanes. Application of this methodology for a straightforward asymmetric synthesis of (-)-bulgecinine is also described.
- Toumi, Mathieu,Couty, Fran?ois,Evano, Gwilherm
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p. 1175 - 1179
(2008/09/18)
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- Allyltrichlorostannane additions to α-amino aldehydes: Application to the total synthesis of the aspartyl protease inhibitors L-682,679, L-684,414, L-685,434, and L-685,458
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The hydroxyethylene dipeptide isosteres L-682,679, L-684,414, L-685,434, and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-amino aldehyde, followed by hydroboration of the corresponding 1,2-
- Dias, Luiz C.,Diaz, Gaspar,Ferreira, Andrea A.,Meira, Paulo R. R.,Ferreira, Edílson
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p. 603 - 622
(2007/10/03)
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- Stereoselective synthesis of the antifungal antibiotic (+)-preussin
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A concise total synthesis of enantiopure (+)-preussin (1) from L- phenylalanine (3) is described. The key steps involve i) syn-selective formation of the 1,2-amino alcohol fragment 2, via chelation controlled addition of allylmagnesium bromide to N-Boc-phenylalaninal, and ii) L- selectride mediated stereoselective reduction of the ketone 8 to the alcohol derivative 9 with the required stereochemistry for final cyclization.
- Veeresa,Datta, Apurba
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p. 15673 - 15678
(2007/10/03)
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- Ring-closing metathesis strategy to unsaturated γ- and δ-lactones: Synthesis of hydroxyethylene isostere for protease inhibitors
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Ring-closing olefin metathesis of acrylates derived from allylic and homo allylic alcohols in the presence of the Grubbs' catalyst (10-15 mol%) and titanium isopropoxide (0.3-3 equiv) provided ready access to α, β- unsaturated γ and δ-lactones and an important dipeptide isostere intermediate.
- Ghosh, Arun K.,Cappiello, John,Shin, Dongwoo
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p. 4651 - 4654
(2007/10/03)
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- CrCl2 mediated addition of allylic halides or phosphates to N-protected α-amino aldehydes. Stereocontrolled synthesis of a new core for C2 symmetric HIV-protease inhibitors
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The addition of γ-monosubstituted allylchromium(III) reagents to N-protected α-amino aldehydes proceeds in a stereoconvergent manner in contrast with the case of the unsubstituted reagents, where the stereoselectivity depends on the nature of the group bo
- Ciapetti, Paola,Falorni, Massimo,Taddei, Maurizio
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p. 7379 - 7390
(2007/10/03)
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- Addition of Allylic Metals to α-Aminoaldehydes. Application to the Synthesis of Statine, Ketomethylene and Hydroxyethylene Dipeptide Isosteres
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A general and stereoselective method to statine, ketomethylene and hydroxyethylene dipeptide isosteres is described.The key reaction is the diastereoselective allyl metal addition to α-aminoaldehydes.
- Prasad, J. V. N. Vara,Rich, Daniel H.
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p. 1803 - 1806
(2007/10/02)
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