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Chapter III Stereoselective Total synthesis of Nonenolide
141
4. Farooq, A.; Gordon, J.; Hanson, J. R.; Takahashi, J. A. Phytochemistry 1995, 38,
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Chapter III Stereoselective Total synthesis of Nonenolide
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Prabhakar, P.; Rajaram, S.; Reddy, D. K.; Shekhar, V.; Venkateswarlu, Y.
Tetrahedron: Asymmetry 2010, 21, 216.
Chapter III Stereoselective Total synthesis of Nonenolide
143
-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
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
HOOPMB
Fig. 3.02:
13C NMR (75 MHz, CDCl3) spectrum of compound 72
Chapter III Stereoselective Total synthesis of Nonenolide
144
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
OPMB
OH
HO
Fig. 3.03:
1H NMR (300 MHz, CDCl3) spectrum of compound 73
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
OPMB
OH
HO
Fig. 3.04:
13C NMR (75 MHz, CDCl3) spectrum of compound 73
Chapter III Stereoselective Total synthesis of Nonenolide
145
Chapter III Stereoselective Total synthesis of Nonenolide
146
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
OPMB
OH
Fig. 3.07:
1H NMR (300 MHz, CDCl3) spectrum of compound 74
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
OPMB
OH
Fig. 3.08:
13C NMR (75 MHz, CDCl3) spectrum of compound 74
Chapter III Stereoselective Total synthesis of Nonenolide
147
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
OPMB
OTBS
Fig. 3.10:
1H NMR (300 MHz, CDCl3) spectrum of compound 75
Chapter III Stereoselective Total synthesis of Nonenolide
148
-10-1000101020203030404050506060707080809090100100110110120120130130140140150150160160170170
OPMB
OTBS
Fig. 3.11:
13C NMR (75 MHz, CDCl3) spectrum of compound 75
Chapter III Stereoselective Total synthesis of Nonenolide
149
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
OH
OTBS
Fig. 3.13:
1H NMR (300 MHz, CDCl3) spectrum of compound 76
00101020203030404050506060707080809090100100110110120120
OH
OTBS
Fig. 3.14:
13C NMR (75 MHz, CDCl3) spectrum of compound 76
Chapter III Stereoselective Total synthesis of Nonenolide
150
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
OTBS
OH
OH
Fig. 3.15:
1H NMR (300 MHz, CDCl3) spectrum of compound 77
-10-1000101020203030404050506060707080809090100100110110120120130130140140150150
OTBS
OH
OH
Fig. 3.16:
13C NMR (75 MHz, CDCl3) spectrum of compound 77
Chapter III Stereoselective Total synthesis of Nonenolide
151
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
OTBS
OPMB
OH
Fig. 3.18:
1H NMR (300 MHz, CDCl3) spectrum of compound 78
Chapter III Stereoselective Total synthesis of Nonenolide
152
-10-1000101020203030404050506060707080809090100100110110120120130130140140150150160160170170
OTBS
OPMB
OH
Fig. 3.19:
13C NMR (75 MHz, CDCl3) spectrum of compound 78
Chapter III Stereoselective Total synthesis of Nonenolide
153
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
OTBS
OPMB
Fig. 3.22:
1H NMR (300 MHz, CDCl3) spectrum of compound 79
Chapter III Stereoselective Total synthesis of Nonenolide
154
-10-1000101020203030404050506060707080809090100100110110120120130130140140150150160160170170
OTBS
OPMB
Fig. 3.23:
13C NMR (75 MHz, CDCl3) spectrum of compound 79
Chapter III Stereoselective Total synthesis of Nonenolide
155
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
OH
OPMB
Fig. 3.26:
1H NMR (300 MHz, CDCl3) spectrum of compound 80
Chapter III Stereoselective Total synthesis of Nonenolide
156
00101020203030404050506060707080809090100100110110120120130130140140150150160160
OH
OPMB
Fig. 3.27:
13C NMR (75 MHz, CDCl3) spectrum of compound 80
Chapter III Stereoselective Total synthesis of Nonenolide
157
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
HOOPMB
Fig. 3.30:
1H NMR (300 MHz, CDCl3) spectrum of compound 82
Chapter III Stereoselective Total synthesis of Nonenolide
158
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
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
Chapter III Stereoselective Total synthesis of Nonenolide
159
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
PMBO
OH
OH
Fig. 3.33:
13C NMR (75 MHz, CDCl3) spectrum of compound 83
Chapter III Stereoselective Total synthesis of Nonenolide
160
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
O
Fig. 3.35:
1H NMR (300 MHz, CDCl3) spectrum of compound 84
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
PMBO
O
Fig. 3.36:
13C NMR (75 MHz, CDCl3) spectrum of compound 84
Chapter III Stereoselective Total synthesis of Nonenolide
161
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
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170
PMBO
OH
Fig. 3.38:
13C NMR (75 MHz, CDCl3) spectrum of compound 85
Chapter III Stereoselective Total synthesis of Nonenolide
162
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
OTBS
Fig. 3.40:
1H NMR (300 MHz, CDCl3) spectrum of compound 86
Chapter III Stereoselective Total synthesis of Nonenolide
163
-10-1000101020203030404050506060707080809090100100110110120120130130140140150150160160170170
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
Chapter III Stereoselective Total synthesis of Nonenolide
164
00101020203030404050506060707080809090100100110110120120130130140140150150
HO
OTBS
Fig. 3.43:
13C NMR (75 MHz, CDCl3) spectrum of compound 87
Chapter III Stereoselective Total synthesis of Nonenolide
165
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
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
Chapter III Stereoselective Total synthesis of Nonenolide
166
0.00.00.50.51.01.01.51.52.02.02.52.53.03.03.53.54.04.04.54.55.05.05.55.56.06.06.56.57.07.07.57.58.08.0
O
OPMB
O OTBS
Fig. 3.48:
1H NMR (300 MHz, CDCl3) spectrum of compound 89
Chapter III Stereoselective Total synthesis of Nonenolide
167
00252550507575100100125125150150175175
O
OPMB
O OTBS
Fig. 3.49:
13C NMR (75 MHz, CDCl3) spectrum of compound 89
Chapter III Stereoselective Total synthesis of Nonenolide
168
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. 3.52:
1H NMR (300 MHz, CDCl3) spectrum of compound 90
Chapter III Stereoselective Total synthesis of Nonenolide
169
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170180180
O
OPMB
O OH
Fig. 3.53:
13C NMR (75 MHz, CDCl3) spectrum of compound 90
Chapter III Stereoselective Total synthesis of Nonenolide
170
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
Chapter III Stereoselective Total synthesis of Nonenolide
171
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170180180
O
OPMB
O
OH
Fig. 3.57:
13C NMR (75 MHz, CDCl3) spectrum of compound 91
Chapter III Stereoselective Total synthesis of Nonenolide
172
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
Chapter III Stereoselective Total synthesis of Nonenolide
173
00101020203030404050506060707080809090100100110110120120130130140140150150160160170170180180
O
OH
O
OH
Fig. 3.61:
13C NMR (75 MHz, CD3OD) spectrum of compound 37
Chapter III Stereoselective Total synthesis of Nonenolide
174