(1)Tesi doctoral Departament de Química Orgànica “Aplicacions sintètiques dels adductes de Pauson-Khand del norbornadiè

Tesi doctoral

Departament de Química Orgànica

“Aplicacions sintètiques dels adductes de Pauson-Khand del norbornadiè. Aproximació a

la síntesi de prostaglandines i fitoprostans.”

Agustí Lledó Ponsati

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl₃)

TMS

H

H

1

TMS

O

H H

9

13C-RMN (100 MHz, CDCl3)

1H-RMN (400 MHz, CDCl₃)

TMS

O

H₁ H₂

H₄ H₃

2D NOESY (400 MHz, CDCl₃) 1

2

3

4

6 5

O

H H TMS

39

13C-RMN (100 MHz, CDCl₃)

1H-RMN (400 MHz, CDCl3)

H₄ O

H₃ H₇ Si

H₈

H₁ i-Pr

H₂ Me

Me Me

H₅

H₆

2D NOESY (400 MHz, CDCl₃) i-Pr (CH)

i-Pr (CH₃)

Me₃Si

7 8

2

4 1 3 6

5

1H-RMN (400 MHz, CDCl₃)

13C-RMN (100 MHz, CDCl₃)

O

H H

32

H H

38

13C-RMN (100 MHz, CDCl₃)

1H-RMN (400 MHz, CDCl3)

O

H H

49

1H-RMN (400 MHz, CDCl₃)

13C-RMN (100 MHz, CDCl3)

1H-RMN (400 MHz, CDCl₃)

13C-RMN (100 MHz, CDCl₃)

H H

NC

61

H H

OHC O O

64

1H-RMN (400 MHz, CDCl₃)

13C-RMN (100 MHz, CDCl3)

O

TMSH

66

13C-RMN (100 MHz, CDCl₃)

1H-RMN (400 MHz, CDCl₃)

O

H H TMS

HO

65

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl3)

13C-RMN (100 MHz, CDCl₃)

1H-RMN (400 MHz, CDCl₃)

H H

OTIPS 97

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl3)

H O OH C₅H₁₁

OH 70

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl₃)

O

H H

C₄H₉

107

O

H TMS H

C₅H₁₁

OTIPS

79

1H-RMN (400 MHz, CDCl₃)

13C-RMN (100 MHz, CDCl₃)

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl3)

H H

OTBDPS MeOOC

92

O

H

H OTBS

OTIPS

102

13C-RMN (100 MHz, CDCl3)

1H-RMN (400 MHz, CDCl3)

O

H H

COOMe

OH 105

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl3)

O

H H

COOMe C₅H₁₁

O 106

1H-RMN (400 MHz, CDCl₃)

13C-RMN (100 MHz, CDCl₃)

O

COOMe OH

111

1H-RMN (400 MHz, CDCl3)

13C-RMN (100 MHz, CDCl₃)

O TMS

132

13C-RMN (100 MHz, CDCl3)

1H-RMN (400 MHz, CDCl3)