Chapter III Stereoselective Total synthesis of...
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4. Farooq, A.; Gordon, J.; Hanson, J. R.; Takahashi, J. A. Phytochemistry 1995, 38,
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5. Ackland, M. J.; Hanson, J. R.; Hitchcock, P. B.; Ratcliffe, A. H. J. Chem Soc.,
Perkin Trans. 1 1985, 843.
6. Moore, B. P.; Brown, W. V. Aust. J. Chem. 1976, 29, 1365.
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11. (a) Grabley, S.; Granzer, E.; Hutter, K.; Ludwig, D.; Mayer, M.; Thiericke, R.;
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18. Mohapatra, D. K.; Ramesh, D. K.; Giardello, M. A.; Chorghade, M. S.; Gurjara,
M. K.; Grubbs, R. H. Tetrahedron Lett. 2007, 48, 2621.
19. Rama Rao, A. V.; Murthy, V. S.; Sharma, G. V. M. Tetrahedron Lett. 1995, 36,
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20. Liu, J.; Zhang, L.; He, J.; He, L.; Ma, B.; Pan, X.; She, X. Tetrahedron:
Asymmetry 2008, 19, 906.
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J. A.; Simpson, T. J.; Willis, C. L.; Lindell, S. D. Tetrahedron: Asymmetry 1994,
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24. a) Donohoe, T. J.; Lindsay-Scott, P. J.; Parker, J. S.; Callens, C. K. A. Org. Lett.
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W. C. J. Am. Chem. Soc. 2003, 125, 10808.
25. (a) Mangion, I. K.; Macmillan, D. W. C. J. Am. Chem. Soc. 2005, 127, 3696; (b)
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Yamaguchi, J.; Hibino, K.; Shoji, M. Tetrahedron Lett. 2003, 44, 8293.
26. (a) Reddy, C. R.; Dilipkumar, U.; Reddy, M. D.; Rao, N. N. Org. Biomol. Chem.
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27. (a) Furstner, A.; Radkowski, K. Chem. Commun. 2001, 671; (b) Nagaiah, K.;
Sreenu, D.; Rao, S. S.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 7173.
28. (a) M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 1, 953. (b)
Prabhakar, P.; Rajaram, S.; Reddy, D. K.; Shekhar, V.; Venkateswarlu, Y.
Tetrahedron: Asymmetry 2010, 21, 216.
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-0.5-0.50.00.00.50.51.01.01.51.52.02.02.52.53.03.03.53.54.04.04.54.55.05.05.55.56.06.06.56.57.07.07.57.58.08.0
HOOPMB
Fig. 3.01:
1H NMR (300 MHz, CDCl3) spectrum of compound 72
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HOOPMB
Fig. 3.02:
13C NMR (75 MHz, CDCl3) spectrum of compound 72
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OPMB
OH
HO
Fig. 3.03:
1H NMR (300 MHz, CDCl3) spectrum of compound 73
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OPMB
OH
HO
Fig. 3.04:
13C NMR (75 MHz, CDCl3) spectrum of compound 73
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OPMB
OH
Fig. 3.07:
1H NMR (300 MHz, CDCl3) spectrum of compound 74
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OPMB
OH
Fig. 3.08:
13C NMR (75 MHz, CDCl3) spectrum of compound 74
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OPMB
OTBS
Fig. 3.10:
1H NMR (300 MHz, CDCl3) spectrum of compound 75
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-10-1000101020203030404050506060707080809090100100110110120120130130140140150150160160170170
OPMB
OTBS
Fig. 3.11:
13C NMR (75 MHz, CDCl3) spectrum of compound 75
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OH
OTBS
Fig. 3.13:
1H NMR (300 MHz, CDCl3) spectrum of compound 76
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OH
OTBS
Fig. 3.14:
13C NMR (75 MHz, CDCl3) spectrum of compound 76
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OTBS
OH
OH
Fig. 3.15:
1H NMR (300 MHz, CDCl3) spectrum of compound 77
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OTBS
OH
OH
Fig. 3.16:
13C NMR (75 MHz, CDCl3) spectrum of compound 77
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OTBS
OPMB
OH
Fig. 3.18:
1H NMR (300 MHz, CDCl3) spectrum of compound 78
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OTBS
OPMB
OH
Fig. 3.19:
13C NMR (75 MHz, CDCl3) spectrum of compound 78
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OTBS
OPMB
Fig. 3.22:
1H NMR (300 MHz, CDCl3) spectrum of compound 79
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OTBS
OPMB
Fig. 3.23:
13C NMR (75 MHz, CDCl3) spectrum of compound 79
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OH
OPMB
Fig. 3.26:
1H NMR (300 MHz, CDCl3) spectrum of compound 80
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OH
OPMB
Fig. 3.27:
13C NMR (75 MHz, CDCl3) spectrum of compound 80
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HOOPMB
Fig. 3.30:
1H NMR (300 MHz, CDCl3) spectrum of compound 82
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HOOPMB
Fig. 3.31:
13C NMR (75 MHz, CDCl3) spectrum of compound 82
0.00.00.50.51.01.01.51.52.02.02.52.53.03.03.53.54.04.04.54.55.05.05.55.56.06.06.56.57.07.07.57.5
PMBO
OH
OH
Fig. 3.32:
1H NMR (300 MHz, CDCl3) spectrum of compound 83
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PMBO
OH
OH
Fig. 3.33:
13C NMR (75 MHz, CDCl3) spectrum of compound 83
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PMBO
O
Fig. 3.35:
1H NMR (300 MHz, CDCl3) spectrum of compound 84
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PMBO
O
Fig. 3.36:
13C NMR (75 MHz, CDCl3) spectrum of compound 84
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0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5
PMBO
OH
Fig. 3.37:
1H NMR (300 MHz, CDCl3) spectrum of compound 85
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PMBO
OH
Fig. 3.38:
13C NMR (75 MHz, CDCl3) spectrum of compound 85
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PMBO
OTBS
Fig. 3.40:
1H NMR (300 MHz, CDCl3) spectrum of compound 86
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PMBO
OTBS
Fig. 3.41:
13C NMR (75 MHz, CDCl3) spectrum of compound 86
0.00.00.50.51.01.01.51.52.02.02.52.53.03.03.53.54.04.04.54.55.05.05.55.56.06.06.56.57.07.07.57.5
HO
OTBS
Fig. 3.42:
1H NMR (300 MHz, CDCl3) spectrum of compound 87
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HO
OTBS
Fig. 3.43:
13C NMR (75 MHz, CDCl3) spectrum of compound 87
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HO
OTBSO
Fig. 3.45:
1H NMR (300 MHz, CDCl3) spectrum of compound 88
00252550507575100100125125150150175175
HO
OTBSO
Fig. 3.46:
13C NMR (75 MHz, CDCl3) spectrum of compound 88
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O
OPMB
O OTBS
Fig. 3.48:
1H NMR (300 MHz, CDCl3) spectrum of compound 89
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O
OPMB
O OTBS
Fig. 3.49:
13C NMR (75 MHz, CDCl3) spectrum of compound 89
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O
OPMB
O OH
Fig. 3.52:
1H NMR (300 MHz, CDCl3) spectrum of compound 90
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O
OPMB
O OH
Fig. 3.53:
13C NMR (75 MHz, CDCl3) spectrum of compound 90
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0.00.00.50.51.01.01.51.52.02.02.52.53.03.03.53.54.04.04.54.55.05.05.55.56.06.06.56.57.07.07.57.5
O
OPMB
O
OH
Fig. 3.56:
1H NMR (300 MHz, CDCl3) spectrum of compound 91
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O
OPMB
O
OH
Fig. 3.57:
13C NMR (75 MHz, CDCl3) spectrum of compound 91
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0.00.00.50.51.01.01.51.52.02.02.52.53.03.03.53.54.04.04.54.55.05.05.55.56.06.06.56.57.07.0
O
OH
O
OH
Fig. 3.60:
1H NMR (300 MHz, CD3OD) spectrum of compound 37
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O
OH
O
OH
Fig. 3.61:
13C NMR (75 MHz, CD3OD) spectrum of compound 37
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