A Short Synthesis of Fusaric Acid and Analogues

References

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• 5d was isolated in low yield as yellow oil readily eliminating dimethylamine on standing at r. t. for a few days. 1H-NMR(CDCl3): 5.82 (1H, s, broad, H-C(6)); 5.34 (1H, t, J1=4 Hz, H-C(3)); 2.87 (2H, d, J1=4 Hz, H2-C(4)); 2.56 (6H, s, (CH3)2N); 1.90 (2H, quart., J2=7 Hz, CH2); 1.0 (3H, t, J2=7 Hz, CH3).
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• 6a: m. p. 72–4° 1H-NMR(CDCl3): 8.33 (1H, s, broad, H-C(6)); 7.38 (1H, s, H-C(4)); 2.27 (6H, s, 2 CH3). 6b: m. p. 56–9° 1H-NMR(CDCl3): 8.35 (1H, s, H-C(6)); 7.38 (1H, s, H-C(4)); 2.70–2.90 (4H, m, 2 CH2); 1.78–1.94 (4H, m, CH2CH2). 6c: m. p. 72–4°; 1H-NMR(CDCl3): 8.60 (1H, s, broad, H-C(6)); 7.66 (2H, s, broad, H-C(4), H-C(3)); 2.50 (3H, s, CH3). 6e: liquid; 1H-NMR(CDCl3): 8.50 (1H, s, broad, H-C(6)); 7.60 (2H, m, H-C(4), H-C(3)); 2.66 (2H, t, J=8 Hz, CH2); 1.60 (2H, m, CH2); 1.36 (2H, sext., J-7.5 Hz, CH2); 0.9 (3H, t, J=7.5 Hz, CH3). 6f: m. p. 47–9°; 1H-NMR(CDCl3); 8.56 (1H, d, broad, J=1.9 Hz, H-C(6)); 7.66 (1H, dd, J1=1.9 Hz, J2=8 Hz, H-C(4)); 7.60 (1H, dd, J2=8 Hz, J3=1 Hz, H-C(3)); 3.0(1H, sept., J4=7Hz, H-C); 1.26 (6H, d, J4=7 Hz, (CH3)2C).
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