References
-
1a
Howard JB.
Nelsestuen GL.
Biochem. Biophys. Res. Commun.
1974,
59:
757
-
1b
Nelsestuen GL.
Zytkovicz TH.
J. Biol. Chem.
1974,
249:
6347
-
1c
Zytkovicz TH.
Nelsestuen GL.
J. Biol. Chem.
1975,
250:
2968
- 2
Stenflo J.
Fernlund P.
Egan W.
Roepstorff P.
Proc. Natl. Acad. Sci. U.S.A.
1974,
71:
2730
- 3
Saito H.
Hirata T.
Tetrahedron Lett.
1987,
28:
4065
- 4 For a recent review, see: Scott JD.
Williams RM.
Chem. Rev.
2002,
102:
1669
-
5a
Märki W.
Opplinger M.
Thanei P.
Schwyzer R.
Helv. Chim. Acta
1977,
60:
798
-
5b
Boggs NT.
Goldsmith B.
Gawley RE.
Koehler KA.
Hiskey RG.
J. Org. Chem.
1979,
44:
2262
-
5c
Cerovsky V.
Jost K.
Collect. Czech. Chem. Commun.
1984,
49:
2562
-
6a
Zee-Cheng RKY.
Olson RE.
Biochem. Biophys. Res. Commun.
1980,
94:
1128
-
6b
Baldwin JE.
North M.
Flinn A.
Moloney MG.
J. Chem. Soc., Chem. Commun.
1988,
12:
828
- 7
Danishefsky S.
Berman E.
Clizbe LA.
Hirama M.
J. Am. Chem. Soc.
1979,
101:
4385
-
8a
Tanaka K.-I.
Yoshifuji S.
Nitta Y.
Chem. Pharm. Bull.
1986,
34:
3879
-
8b
Effenberger F.
Müller W.
Keller R.
Wild W.
Ziegler T.
J. Org. Chem.
1990,
55:
3064
- 9
Weinstein B.
Watrin KG.
Jeff Loie H.
Martin JC.
J. Org. Chem.
1976,
41:
3634
- 10
Dugave C.
Menez A.
J. Org. Chem.
1996,
61:
6067
- 11
Schuerman MA.
Keverline KI.
Hiskey RG.
Tetrahedron Lett.
1995,
36:
825
-
12a
Garner P.
Park JM.
J. Org. Chem.
1987,
52:
2361
-
12b
Garner P.
Park JM.
J. Org. Chem.
1988,
53:
2979
-
12c
Garner P.
Park JM.
Malecki E.
J. Org. Chem.
1988,
53:
4395
-
12d
Angrick M.
Monatsh. Chem.
1985,
116:
645
-
12e
Campbell AD.
Raynham TM.
Taylor RJK.
Synthesis
1998,
1707
-
12f For a review, see: Liang X.
Andersch J.
Bols M.
J. Chem. Soc., Perkin Trans. 1
2001,
2136
-
Recent application in the synthesis of non-proteinogenic amino acid involving a sequence of olefination-hydrogenation of serinal, see:
-
13a
Xing X.
Fichera A.
Kumar K.
Org. Lett.
2001,
3:
1285
-
13b
Ramesh Babu I.
Hamill EK.
Kumar K.
J. Org. Chem.
2004,
69:
5468
- 14
Reetz MT.
Röhrig D.
Angew. Chem., Int. Ed. Engl.
1989,
28:
1706
- 15
Grigg R.
Lansdell MI.
Thornton-Pett M.
Tetrahedron
1999,
55:
2025
- 16
Larcheveque M.
Tamagnan G.
Petit Y.
J. Chem. Soc., Chem. Commun.
1989,
31
- 17
Ma D.
Wu Q.
Tetrahedron Lett.
2000,
41:
9089
- 18
Oikawa Y.
Hirasawa H.
Yonemitsu O.
Tetrahedron Lett.
1978,
1759
- 19
List B.
Castello C.
Synlett
2001,
1687
- 20
Dardennes E.
Kovacs-Kulyassa A.
Renzetti A.
Sapi J.
Laronze J.-Y.
Tetrahedron Lett.
2003,
44:
221
- 21
Hedge JA.
Kruse CW.
Snyder HR.
J. Org. Chem.
1961,
26:
3166
- 22 For a review on Meldrum’s acid, see: Chen BC.
Heterocycles
1991,
32:
529
- 24
Davies JS.
Enjalbal C.
Nguyen C.
Al-Jamri L.
Naumer C.
J. Chem. Soc., Perkin Trans. 1
2000,
2907
23 Compound 2a: [α]D
25 +3.3 (c 1.0, CHCl3). FT-IR (CHCl3): 3432, 3026, 3015, 1733, 1503, 1437, 1368 cm-1. 1H NMR (250 MHz, CDCl3): δ = 6.20 (br s, 1 H), 5.09 (d, 1 H, J = 7.3 Hz), 4.39 (m, 1 H), 3.75 (s, 3 H), 3.74 (s, 3 H), 3.57 (t, 1 H, J = 6.8 Hz), 2.54 (m, 1 H), 2.25 (m, 1 H), 1.43 (s, 9 H). 13C NMR (62.5 MHz, CDCl3): δ = 175.5, 169.0, 155.5, 80.4, 52.8, 51.7, 48.3, 31.1, 28.2 ppm. HRMS: m/z calcd for C13H21NNaO8 [M + Na]: 342.1165; found: 342.1174.
Compound 2b: [α]D
25 -2.5 (c 1.0, CHCl3). FT-IR (CHCl3): 3425, 3016, 2956, 1732, 1509, 1438, 1236, 1199, 1061
cm-1. 1H NMR (300 MHz, CDCl3): δ = 7.35 (m, 5 H), 5.39 (br s, 1 H), 5.11 (s, 2 H), 4.50 (m, 1 H), 3.74 (s, 3 H), 3.70 (s, 3 H), 3.59 (m, 1 H), 2.60 (m, 1 H), 2.27 (m, 1 H). 13C NMR (300 MHz, CDCl3): δ = 175.1, 169.5, 169.1, 156.3, 136.1, 128.8, 128.6, 128.5, 128.3, 128.2, 67.4, 52.9, 52.2, 48.4, 31.2 ppm. HRMS (ESI): m/z calcd for C16H19NNaO8 [M + Na]: 376.1008; found: 376.0993