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DOI: 10.1055/s-0031-1289586
Preparation of α-Hydroxy-β-Fmoc Amino Acids from N-Boc Amino Acids
Publikationsverlauf
Publikationsdatum:
03. November 2011 (online)

Abstract
A general method for the conversion of N-Boc amino acids into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrolysis of the nitrile group, followed by reprotection of the amino acid as the Fmoc derivative.
Key words
N-Boc amino acid - reduction - hydrocyanation - N-Fmoc amino acid
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Han W.Hu Z.Jiang X.Decicco CP. Bioorg. Med. Chem. Lett. 2000, 10: 711 - 4
Tromp RA.Van de Hoeven M.Amore A.Brussee J.Overhand M.Van der Marel GA.Van der Gen A. Tetrahedron: Asymmetry 2001, 12: 1109 - 5
Harbeson SL.Abelleira SM.Akiyama A.Barrett R.Carroll RM.Straub JA.Tkacz JW.Wu C.Musso G. J. Med. Chem. 1994, 37: 2918 - 6
Boger DL.Colletti SL.Honda T.Menezes RF. J. Am. Chem. Soc. 1994, 116: 5607 - 7
Skiles JW.Miao C.Sorcek R.Jacober S.Mui PW.Chow G.Weldon SM.Possanza G.Skoog M.Keirns J.Letts G.Rosenthal AS. J. Med. Chem. 1992, 35: 4795 - 8
Saari WS.Fisher TE. Synthesis 1990, 453 - 9
Tietze LF.Burkhardt O. Synthesis 1994, 1331 - 10
Hamada Y.Shibata M.Sugiura T.Kato S.Shioiri T. J. Org. Chem. 1987, 52: 1252 - 11 For preparation of the Fmoc derivative,
see:
Myers AG.Kung DW.Zhong B. J. Am. Chem. Soc. 2000, 122: 3236 - 12
Veeresa G.Datta A. Tetrahedron Lett. 1998, 39: 3069 - 13
Greenlee WJ.Springer JP.Patchett A. J. Med. Chem. 1989, 32: 165 - 14
Mohan R.Chou Y.-L.Bihovsky R.Lumma WC.Erhardt PW.Shaw KJ. J. Med. Chem. 1991, 34: 2402 - 15
Iizuka K.Kamijo T.Harada H.Akahane K.Kubota T.Shimaoka I.Umeyama H.Kiso Y. Chem. Pharm. Bull. 1988, 36: 2278 - 16
Myers AG.Zhong B.Movassaghi M.Kung DW.Lanman BA.Kwon A. Tetrahedron Lett. 2000, 41: 1359 - 17
Tsuda M.Muraoka Y.Nagai M.Takeuchi T.Aoyagi T. J. Antibiot. 1996, 49: 287 - 19
Bursavich MG.Rich DH. J. Med. Chem. 2002, 45: 541
References
New address: Incyte Corporation, Wilmington, DE, USA.
2New address: Johnson and Johnson Pharmaceutical Research and Development, Welsh and McKean Roads, Spring House, PA, USA.
18Personal communication: Dr. Dan Siesel, Albany Molecular Research Inc.