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Chapter III Stereoselective Total synthesis of Nonenolide

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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

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

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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

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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

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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

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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

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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

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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

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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

Chapter III Stereoselective Total synthesis of Nonenolide

164

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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

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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

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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

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O

OH

O

OH

Fig. 3.61:

13C NMR (75 MHz, CD3OD) spectrum of compound 37

Chapter III Stereoselective Total synthesis of Nonenolide

174