APPENDIX 2

(1)

Appendix 2–Spectra Relevant to Chapter 1 72

APPENDIX 2

Spectra Relevant to Chapter 1:

Evolving Strategies Toward the Synthesis of Curcusone C

(2)

Appendix 3—Spectra Relevant to Chapter 1 128

Figure A3.45 1 H NMR (500 MHz, CDCl3) of compound 27

TfO Figure A2.11 H NMR (500 MHz, CDCl3) of compound 28

(3)

Figure A3.47 ¹³C NMR (126 MHz, CDCl3) of compound 27 Figure A3.46 Infrared spectrum (thin film/NaCl) of compound 27

Figure A2.3 ¹³C NMR (126 MHz, CDCl3) of compound 28 Figure A2.2 Infrared spectrum (Thin Film, NaCl) of compound 28

(4)

Appendix 2–Spectra Relevant to Chapter 1 Appendix 3—Spectra Relevant to Chapter 1 130 75

Figure A3.48 1 H NMR (400 MHz, C6D6) of compound 59

OTBS Figure A2.4 1H NMR (400 MHz, CDCl3) of compound 31

(5)

Figure A3.50 ¹³C NMR (101 MHz, C6D6) of compound 59 Figure A3.49 Infrared spectrum (thin film/NaCl) of compound 59

Figure A2.6 ¹³C NMR (101 MHz, C6D6) of compound 31 Figure A2.5 Infrared spectrum (Thin Film, NaCl) of compound 31

(6)

OH Figure A2.7 1H NMR (400 MHz, C6D6) of compound 87

(7)

Figure A3.53 ¹³C NMR (101 MHz, C₆D₆₃) of compound 60 Figure A3.52 Infrared spectrum (thin film/NaCl) of compound 60

(8)

Figure A3.541 H NMR (400 MHz, C6D6) of compound 61

OOO Figure A2.101H NMR (400 MHz, C6D6) of compound 33

(9)

Figure A3.56 ¹³C NMR (101 MHz, C₆D₆) of compound 61 Figure A3.55 Infrared spectrum (thin film/NaCl) of compound 61

(10)

OOO N2 Figure A2.131H NMR (500 MHz, CDCl3) of compound 34

(11)

(12)

I

O Figure A3.60 1 H NMR (400 MHz, C6D6) of compound ent-64Figure A2.16 1H NMR (400 MHz, C6D6) of compound 38

(13)

Figure A3.62 ¹³C NMR (101 MHz, C6D6) of compound ent-64 Figure A3.61 Infrared spectrum (thin film/NaCl) of compound ent-64

(14)

TBSOO Figure A2.191H NMR (400 MHz, C6D3) of compound 39

(15)

(16)

HOO Figure A2.221H NMR (400 MHz, C6D6) of compound 88

(17)

(18)

Figure A3.691 H NMR (400 MHz, CD2Cl2) of compound 71

OO

O O Figure A2.251H NMR (400 MHz, CD2Cl2) of compound 40

(19)

Figure A2.26 Infrared spectrum (Thin Film, NaCl) of compound 40

Figure A3.71 ¹³C NMR (101 MHz, CD2Cl2) of compound 71 Figure A3.70 Infrared spectrum (thin film/NaCl) of compound 71

Figure A2.27 ¹³C NMR (101 MHz, CD2Cl2) of compound 40

(20)

O

OO O Figure A2.281H NMR (400 MHz, CDCl3) of compound 41

(21)

(22)

O

OO O Figure A2.311H NMR (400 MHz, CDCl3) of compound 42

(23)

(24)

O Br Figure A3.78 1 H NMR (500 MHz, CDCl3) of compound 76 Figure A2.341 H NMR (500 MHz, CDCl3) of compound 43

(25)

Figure A3.80 ¹³C NMR (126 MHz, CDCl₃) of compound 76 Figure A3.79 Infrared spectrum (thin film/NaCl) of compound 76

(26)

Br

OTBS

Br

OTBS Figure A2.371 H NMR (500 MHz, CDCl3) of compound 21

(27)

(28)

BPin

OH Figure A3.87 1 H NMR (400 MHz, CDCl3) of compound 79Figure A2.401H NMR (500 MHz, CDCl3) of compound 44

(29)

(30)

HOTBSO Figure A2.431H NMR (500 MHz, CDCl3) of compound 19

(31)

Figure A3.92 ¹³C NMR (126 MHz, CDCl₃) of compound 80 Figure A3.91 Infrared spectrum (thin film/NaCl) of compound 80

(32)

OTBSO

OO Figure A2.461H NMR (500 MHz, CDCl3) of compound 45

(33)

(34)

Figure A3.961 H NMR (500 MHz, CDCl3) of compound 75

OTBSO

OO N2 Figure A2.491H NMR (500 MHz, CDCl3) of compound 18

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(36)

O

O O OTBS

O

OO TBSO Figure A3.99 1 H NMR (500 MHz, CDCl3) of compound 82Figure A2.521H NMR (500 MHz, CDCl3) of compound 46

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(38)

OO OTBS

O

O TBSO Figure A3.102 1 H NMR (500 MHz, CDCl3) of compound 83 Figure A2.551 H NMR (500 MHz, CDCl3) of compound 47

(39)

(40)

HO H HO

TBSO Figure A3.105 1 H NMR (400 MHz, DMSO-d6) of compound 85Figure A2.58 1H NMR (500 MHz, DMSO-d6) of compound 49

(41)

Figure A3.107 ¹³C NMR (101 MHz, DMSO-d6) of compound 85 Figure A3.106 Infrared spectrum (thin film/NaCl) of compound 85

Figure A2.60 ¹³C NMR (126 MHz, DMSO-d6) of compound 49 Figure A2.59 Infrared spectrum (Thin Film, NaCl) of compound 49

(42)

HO H HO

TBSO Figure A2.611 H NMR (500 MHz, C6D6) of compound 49

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Appendix 3—Spectra Relevant to Chapter 1

171

Figure A3.109 NOESY (600 MHz, C6D6) of compound 85Figure A2.62 NOESY (600 MHz, C6D6) of compound 49

(44)

Appendix 3—Spectra Relevant to Chapter 1 172

Figure A3.110 gCOSY (600 MHz, C6D6) of compound 85Figure A2.631H–1H gCOSY NMR (600 MHz, C6D6) of compound 49

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Appendix 3—Spectra Relevant to Chapter 1 173

Figure A3.111 1 H-13 C HSQC (600 MHz, C6D6) of compound 85Figure A2.641H–13C HSQC NMR (600 MHz, C6D6) of compound 49

(46)

Supporting Information S8

TfO EtO2C

NMR and IR Spectra of New Compounds

1 H NMR (500 MHz, CDCl3) of compound 14 Figure A2.651 H NMR (500 MHz, CDCl3) of compound 60

(47)

(48)

EtO2C

OO 1 H NMR (400 MHz, CDCl3) of compound 12 4

Et2O Figure A2.681 H NMR (500 MHz, CDCl3) of compound 58

(49)

(50)

1 H–13 C HSQC NMR (400 MHz, CDCl3) of compound 12Figure A2.711H–13C HSQC NMR (400 MHz, CDCl3) of compound 58

(51)

O N

OO MeO 1 H NMR (400 MHz, CDCl3) of compound 19 Figure A2.721 H NMR (500 MHz, CDCl3) of compound 67

(52)

(53)

O H

OO 1 H NMR (500 MHz, CDCl3) of compound 20 Figure A2.751 H NMR (500 MHz, CDCl3) of compound 68

(54)

(55)

O H

O 1 H NMR (500 MHz, CDCl3) of compound 11

EtOAcEt2O Figure A2.781 H NMR (500 MHz, CDCl3) of compound 57

(56)

Figure A2.79 Infrared spectrum (Thin Film, NaCl) of compound 57

Figure A2.80 ¹³C NMR (126 MHz, CDCl3) of compound 57

(57)

O

O H

H 1 H NMR (500 MHz, CDCl3) of compound 22

EtOAc Et2O Figure A2.811 H NMR (500 MHz, CDCl3) of compound 63

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(59)

O 1 H NMR (500 MHz, CDCl3) of compound 23 Figure A2.841H NMR (500 MHz, CDCl3) of compound 72

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(61)

O 1 H NMR (400 MHz, CDCl3) of compound 24 Figure A2.871 H NMR (500 MHz, CDCl3) of compound 73

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(63)

1 H–13 C HSQC NMR (400 MHz, CDCl3) of compound 24 Figure A2.90 1H–13C HSQC NMR (400 MHz, CDCl3) of compound 73