LIST OF TABLES

Table A7.3.1. Experimental Details for X-Ray Structure Determination of Bromide 346 ... 321 Table A7.3.2. Crystal Data and Structure Refinement for Bromide 346 ... 322 Table A7.3.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Bromide 346 ... 323 Table A7.3.4. Bond lengths [Å] and angles [°] for Bromide 346 ... 324 Table A7.3.5. Anisotropic displacement parameters (Ųx10³) for Bromide 346 ... 329 Table A7.3.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Bromide 346 ... 330 Table A7.3.7. Torsion angles [°] for Bromide 346 ... 331 Table A7.3.8. Hydrogen bonds for Bromide 346 [Å and °]. ... 334 Table A7.4.1. Experimental Details for X-Ray Structure Determination of Diketone 347 ... 336 Table A7.4.2. Crystal Data and Structure Refinement for Diketone 347 ... 337 Table A7.4.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Diketone 347 ... 338 Table A7.4.4. Bond lengths [Å] and angles [°] for Diketone 347 ... 339 Table A7.4.5. Anisotropic displacement parameters (Ųx10³) for Diketone 347 ... 344 Table A7.4.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Diketone 347 ... 345 Table A7.4.7. Torsion angles [°] for Diketone 347 ... 346 Table A7.4.8. Hydrogen bonds for Diketone 347 [Å and °]. ... 349 Table A7.5.1. Experimental Details for X-Ray Structure Determination of Hemiketal 350 ... 351 Table A7.5.2. Crystal Data and Structure Refinement for Hemiketal 350 ... 352 Table A7.5.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Hemiketal 350 ... 353 Table A7.5.4. Bond lengths [Å] and angles [°] for Hemiketal 350 ... 354 Table A7.5.5. Anisotropic displacement parameters (Ųx10³) for Hemiketal 350 ... 359 Table A7.5.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Hemiketal 350 ... 360 Table A7.5.7. Torsion angles [°] for Hemiketal 350 ... 361 Table A7.5.8. Hydrogen bonds for Hemiketal 350 [Å and °] ... 364

APPENDIX 8

Alternative Synthetic Strategies Toward Ineleganolide

Table A8.2.1. Attempted Olefin Isomerization ... 368

Table A8.7.1.1. Experimental Details for X-Ray Structure Determination of Chloride 367 ... 377 Table A8.7.1.2. Crystal Data and Structure Refinement for Chloride 367 ... 378 Table A8.7.1.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Chloride 367 ... 379 Table A8.7.1.4. Bond lengths [Å] and angles [°] for Chloride 367 ... 380 Table A8.7.1.5. Anisotropic displacement parameters (Ųx10³) for Chloride 367 ... 385 Table A8.7.1.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Chloride 367 ... 386 Table A8.7.1.7. Torsion angles [°] for Chloride 367 ... 387 Table A8.7.1.8. Hydrogen bonds for Chloride 367 [Å and °]. ... 390 Table A8.7.2.1. Experimental Details for X-Ray Structure Determination of Fluoride 369 ... 392 Table A8.7.2.2. Crystal Data and Structure Refinement for Fluoride 369 ... 393 Table A8.7.2.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Fluoride 369 ... 394 Table A8.7.2.4. Bond lengths [Å] and angles [°] for Fluoride 369 ... 395 Table A8.7.2.5. Anisotropic displacement parameters (Ųx10³) for Fluoride 369 ... 400 Table A8.7.2.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Fluoride 369 ... 401 Table A8.7.2.7. Torsion angles [°] for Fluoride 369 ... 402 Table A8.7.2.8. Hydrogen bonds for Fluoride 369 [Å and °]. ... 405

CHAPTER 4

Revised Plan for the Synthesis of Ineleganolide: Alternative Advancement Toward the Asymmetric Total Synthesis of Ineleganolide by Late-Stage Oxidation State Manipulation

Table 4.6.1. Comparison of ¹³C NMR Shifts of Enone 328 and Diene 422 ... 427

APPENDIX 11

X-Ray Crystallography Reports Relevant to Chapter 4

Table A11.1.1. Experimental Details for X-Ray Structure Determination of Epoxide 371 ... 556 Table A11.1.2. Crystal Data and Structure Refinement for Epoxide 371 ... 557 Table A11.1.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Epoxide 371 ... 558

Table A11.1.4. Bond lengths [Å] and angles [°] for Epoxide 371 ... 559 Table A11.1.5. Anisotropic displacement parameters (Ųx10³) for Epoxide 371 ... 564 Table A11.1.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³)for Epoxide 371 ... 565 Table A11.1.7. Torsion angles [°] for Epoxide 371 ... 566 Table A11.1.8. Hydrogen bonds for Epoxide 371 [Å and °]. ... 569 Table A11.2.1. Experimental Details for X-Ray Structure Determination

of 2H-Ineleganolide (373) ... 571 Table A11.2.2. Crystal Data and Structure Refinement for 2H-Ineleganolide (373) ... 572 Table A11.2.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for 2H-Ineleganolide (373) ... 573 Table A11.2.4. Bond lengths [Å] and angles [°] for 2H-Ineleganolide (373) ... 575 Table A11.2.5. Anisotropic displacement parameters (Ųx10³) for 2H-Ineleganolide (373) ... 585 Table A11.2.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for 2H-Ineleganolide (373) ... 587 Table A11.2.7. Torsion angles [°] for 2H-Ineleganolide (373) ... 589 Table A11.2.8. Hydrogen bonds for 2H-Ineleganolide (373) [Å and °]. ... 593 Table A11.3.1. Experimental Details for X-Ray Structure Determination of Diketone 375 ... 595 Table A11.3.2. Crystal Data and Structure Refinement for Diketone 375 ... 596 Table A11.3.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Diketone 375 ... 597 Table A11.3.4. Bond lengths [Å] and angles [°] for Diketone 375 ... 598 Table A11.3.5. Anisotropic displacement parameters (Ųx10³) for Diketone 375 ... 603 Table A11.3.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Diketone 375 ... 604 Table A11.3.7. Torsion angles [°] for Diketone 375 ... 605 Table A11.3.8. Hydrogen bonds for Diketone 375 [Å and °]. ... 607

APPENDIX 13

X-Ray Crystallography Reports Relevant to Chapter 5

Table A13.1.1. Crystal Data and Structure Refinement for Thioimidate 440 ... 714 Table A13.1.2. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Thioimidate Thioimidate 440 ... 716 Table A13.1.3. Bond lengths [Å] and angles [°] for Thioimidate 440 ... 717 Table A13.1.4. Anisotropic displacement parameters (Ųx10³) for Thioimidate 440 ... 722

Table A13.1.5. Hydrogen coordinates (x10³) and isotropic displacement

parameters (Ųx10³) for Thioimidate 440 ... 723 Table A13.2.1. Crystal Data and Structure Refinement for Amidine (R)-450•HBr ... 725 Table A13.2.2. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Amidine (R)- 450•HBr ... 727 Table A13.2.3. Bond lengths [Å] and angles [°] for Amidine (R)- 450•HBr ... 733 Table A13.2.4. Anisotropic displacement parameters (Ųx10³) for Amidine (R)- 450•HBr ... 762 Table A13.2.5. Hydrogen coordinates (x10³) and isotropic displacement

parameters (Ųx10³) for Amidine (R)- 450•HBr ... 768

CHAPTER 6

Stereoselective Lewis Acid Mediated (3 + 2) Cycloadditions of N-H- and N- Sulfonylaziridines with Heterocumulenes

Table 6.2.1. Optimization of Reaction Conditions ... 776 Table 6.4.1. N-Substitution Scope of Isothiocyanate (3 + 2) Cycloaddition ... 779 Table 6.7.1. Optimization of Stereoselective Reaction Conditions ... 783 Table 6.9.1. N-Substitution Scope of Stereoselective Isothiocyanate (3 + 2) Cycloaddition ... 785

APPENDIX 15

X-Ray Crystallography Reports Relevant to Chapter 6

Table A15.1.1. Experimental Details for X-Ray Structure Determination of Thiazolidine (S)-522 .... 953 Table A15.1.2. Crystal Data and Structure Refinement for Thiazolidine (S)-522 ... 953 Table A15.1.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Thioimidate Thiazolidine (S)-522 ... 955 Table A15.1.4. Bond lengths [Å] and angles [°] for Thiazolidine (S)-522 ... 958 Table A15.1.5. Anisotropic displacement parameters (Ųx10³) for Thiazolidine (S)-522 ... 970 Table A15.1.6. Hydrogen coordinates (x10³) and isotropic displacement

parameters (Ųx10³) for Thiazolidine (S)-522 ... 973 Table A15.2.1. Experimental Details for X-Ray Structure Determination of Thiazolidine 536 ... 976 Table A15.2.2. Crystal Data and Structure Refinement for Thiazolidine 536 ... 977 Table A15.2.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Thioimidate Thiazolidine 536 ... 978 Table A15.2.4. Bond lengths [Å] and angles [°] for Thiazolidine 536 ... 980

Table A15.2.5. Anisotropic displacement parameters (Ųx10³) for Thiazolidine 536 ... 987 Table A15.2.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³)for Thiazolidine 536 ... 989 Table A15.3.1. Experimental Details for X-Ray Structure Determination

of Imidazolidinium 590•(ZnBr3•MeOH) ... 992 Table A15.3.2. Crystal Data and Structure Refinement for

Imidazolidinium 590•(ZnBr3•MeOH) ... 993 Table A15.3.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Thioimidate Imidazolidinium 590•(ZnBr3•MeOH) ... 995 Table A15.3.4. Bond lengths [Å] and angles [°] for Imidazolidinium 590•(ZnBr₃•MeOH) ... 997 Table A15.3.5. Anisotropic displacement parameters (Ųx10³) for

Imidazolidinium 590•(ZnBr3•MeOH) ... 1005 Table A15.3.6. Hydrogen coordinates (x10⁴) and isotropic displacement parameters

(Ųx10³) for Imidazolidinium 590•(ZnBr3•MeOH) ... 1007 Table A15.3.7. Hydrogen bonds for Imidazolidinium 590•(ZnBr3•MeOH) [Å and °]. ... 1009 Table A15.4.1. Experimental Details for X-Ray Structure

Determination of Imidazolidine 550 ... 1011 Table A15.4.2. Crystal Data and Structure Refinement for Imidazolidine 550 ... 1012 Table A15.4.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Thioimidate Imidazolidine 550 ... 1013 Table A15.4.4. Bond lengths [Å] and angles [°] for Imidazolidine 550 ... 1015 Table A15.4.5. Anisotropic displacement parameters (Ųx10³) for Imidazolidine 550 ... 1024 Table A15.4.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Imidazolidine 550 ... 1026 Table A15.5.1. Experimental Details for X-Ray Structure Determination of Oxazolidine 591 ... 1029 Table A15.5.2. Crystal Data and Structure Refinement for Oxazolidine 591 ... 1030 Table A15.5.3. Atomic coordinates (x 10⁴) and equivalent isotropic displacement

parameters (Ųx 10³) for Thioimidate Oxazolidine 591 ... 1032 Table A15.5.4. Bond lengths [Å] and angles [°] for Oxazolidine 591 ... 1034 Table A15.5.5. Anisotropic displacement parameters (Ųx10³) for Oxazolidine 591 ... 1043 Table A15.5.6. Hydrogen coordinates (x10⁴) and isotropic displacement

parameters (Ųx10³) for Oxazolidine 591 ... 1045

APPENDIX 18

Notebook Cross-Reference for New Compounds

Table A18.2.1. Notebook Cross-Reference for Compounds in Chapter 2 ... 1065 Table A18.2.2. Notebook Cross-Reference for Compounds in Appendix 3 ... 1066 Table A18.2.3. Notebook Cross-Reference for Compounds in Chapter 3 ... 1067 Table A18.2.4. Notebook Cross-Reference for Compounds in Chapter 4 ... 1068 Table A18.2.5. Notebook Cross-Reference for Compounds in Chapter 5 ... 1070 Table A18.2.6. Notebook Cross-Reference for Compounds in Chapter 6 ... 1072 Table A18.2.7. Notebook Cross-Reference for Compounds in Appendix 16 ... 1074