TABLE OF CONTENTS SEARCH TEXT V.LIST OF ABBREVIATIONS Abbreviation Chemical Name Chemical Structure 18-cr-6 18-crown-6 Ac acetyl acac acetylacetonyl R AA asymmetric aminohydroxylation AD asymmetric dihydroxylation ad adamantyl 店 ADDP 1.1-(azodicarbonyl)dipiperidine 020 ADMET acyclic diene metathesis polymerization acaen N.N'-bis(1-methyl-3-oxobutylidene)ethylenediamine 人双 AIBN 2.2-azo bisisobutyronitrile X Alloc allyloxycarbonyl 人 Am amyl(n-pentyl) 人人 An p-anisyl 0 ANRORC anionic ring-opening ring-closing ag aqueous AQN anthraquinone Ar aryl(substituted aromatic ring) NA
TABLE OF CONTENTS SEARCH TEXT xvii V. LIST OF ABBREVIATIONS Abbreviation Chemical Name Chemical Structure 18-Cr-6 18-crown-6 O O O O O O Ac acetyl O acac acetylacetonyl O O AA asymmetric aminohydroxylation NA AD asymmetric dihydroxylation NA ad adamantyl ADDP 1,1'-(azodicarbonyl)dipiperidine N N N O O N ADMET acyclic diene metathesis polymerization NA acaen N,N’-bis(1-methyl-3-oxobutylidene)ethylenediamine N N O O AIBN 2,2'-azo bisisobutyronitrile N N N N Alloc allyloxycarbonyl OO Am amyl (n-pentyl) An p-anisyl O ANRORC anionic ring-opening ring-closing NA aq aqueous NA AQN anthraquinone O O Ar aryl (substituted aromatic ring) NA
SEANCH TEXT Abbreviation Chemical Name Chemical Structure ATD aluminum tris(2.6-di-tert-butyl-4-methylphenoxide) atm 1 atmosphere=10Pa (pressure) ATPH aluminum tris(2.6-diphenylphenoxide) BBN(9-BBN) 9-borabicyclo[3.3.1]nonane(9-BBN) 马 -8 9-borabicyclo[3.3.1]nonyl 风 BCME bis(chloromethyDether c人oa BCN N-benzyloxycarbonyloxy-5-norbomnene-2.3- dicarboximide 文 BDPP (2R,4R)or(2S,4S)bis(diphenylphosphino)pentane 黑 BER borohydride exchange resin BHT 2.6-dj-t-butyl-p-cresol(butylated hydroxytoluene) BICP 品根 BINAL-H .-diydxy-1mamim 苏 BINAP 2.2-bis(diphenylphosphino)-1.1-binaphthyl 舒
TABLE OF CONTENTS SEARCH TEXT xviii Abbreviation Chemical Name Chemical Structure ATD aluminum tris(2,6-di-tert-butyl-4-methylphenoxide) Al O 3 atm 1 atmosphere = 105 Pa (pressure) NA ATPH aluminum tris(2,6-diphenylphenoxide) O Ph Ph Al 3 BBN (9-BBN) 9-borabicyclo[3.3.1]nonane (9-BBN) B H B 9-borabicyclo[3.3.1]nonyl B BCME bis(chloromethyl)ether Cl Cl O BCN N-benzyloxycarbonyloxy-5-norbornene-2,3- dicarboximide O N O O O O BDPP (2R, 4R) or (2S, 4S) bis(diphenylphosphino)pentane (R) (R) Ph2P PPh2 BER borohydride exchange resin NA BHT 2,6-di-t-butyl-p-cresol (butylated hydroxytoluene) OH BICP 2(R)-2’(R)-bis(dipenylphosphino)-1(R),1’(R)- dicyclopentane (R) (R) (R) (R) Ph2P PPh2 BINAL-H 2,2'-dihydroxy-1,1'-binaphthyl lithium aluminum hydride O O Al H H Li BINAP 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl PPh2 PPh2
TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure BINOL 1.1-bi-2.2'-naphthol 等 Bip biphenyl-4-sulfonyl 00 bipy 2.2-bipyridyl O BLA Bronsted acid assisted chiral Lewis acid bmin 1-butyl-3-methylimidazolium cation O BMS Borane-dimethy sulfide complex HB.SMe, Bn benzyl BNAH 1-benzy-1.4-dihydronicotinamide crok BOB 4-benzyloxybutyryl 人人O Boc t-butoxycarbonyl X BOM benzyloxymethyl Ro BOP-cI s(2-ox-oxazidinyl)phosphinic chloride 8 bp boiling point BPD bis(pinacolatodiboron 书牛 BPO benzoyl peroxide BPS (TBDPS t-butyldiphenyisilyl 0+0
TABLE OF CONTENTS SEARCH TEXT xix Abbreviation Chemical Name Chemical Structure BINOL 1,1'-bi-2,2'-naphthol OH OH Bip biphenyl-4-sulfonyl S O O bipy 2,2'-bipyridyl N N BLA Brönsted acid assisted chiral Lewis acid NA bmin 1-butyl-3-methylimidazolium cation N N BMS Borane-dimethyl sulfide complex H3B SMe2 Bn benzyl BNAH 1-benzyl-1,4-dihydronicotinamide N O NH2 BOB 4-benzyloxybutyryl O O Boc t-butoxycarbonyl O O BOM benzyloxymethyl O BOP-Cl bis(2-oxo-3-oxazolidinyl)phosphinic chloride P O Cl O N O O N O bp boiling point NA BPD bis(pinacolato)diboron O O B B O O BPO benzoyl peroxide O O Ph O Ph O BPS (TBDPS) t-butyldiphenylsilyl Si
TABLE OF CONTENTS SEANCH TEXT Abbreviation Chemical Name Chemical Structure BQ benzoquinone -G-o Bs 4ronmcbeiesuioyl 10 BSA N.O-bis(trimethylsilyl)acetamide 4x BSA Bovine serum albumin NA Bt 1-or 2-benzotriazolyl o BTAF benzyltrimethylammonium fluoride &0 BTEA 义0 BTEAC benzyltriethylammonium chloride 义0 BTFP 3-bromo-1.1.1-trifuoro-propan-2-one 汁 BTMA benzyltrimethylammonium 义0 BTMSA bis(trimethylsilyl)acetylene + BTS HA BTSA oO BTSP is(trimethylsilyl)peroxide Bz benzoyl -0 Bu("Bu) n-butyl c cyclo NA
TABLE OF CONTENTS SEARCH TEXT xx Abbreviation Chemical Name Chemical Structure BQ benzoquinone O O Bs brosyl = (4-bromobenzenesulfonyl) S Br O O BSA N,O-bis(trimethylsilyl)acetamide O Si N Si BSA Bovine serum albumin NA Bt 1- or 2-benzotriazolyl N N N BTAF benzyltrimethylammonium fluoride N F BTEA benzyltriethylammonium N BTEAC benzyltriethylammonium chloride N Cl BTFP 3-bromo-1,1,1-trifluoro-propan-2-one O F F F Br BTMA benzyltrimethylammonium N BTMSA bis(trimethylsilyl) acetylene Si Si BTS bis(trimethylsilyl) sulfate S O O O O Si Si BTSA benzothiazole 2-sulfonic acid S N S O O HO BTSP bis(trimethylsilyl) peroxide O Si O Si Bz benzoyl O Bu (n Bu) n-butyl c cyclo NA
TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure ca CA a cerium(IV)ammonium nitrate(cericammonium CAN nitrate) CoNH.YNO.k cat. catalytic CB catecholborane o CBS Corey-Bakshi-Shibata reagent C设 cbz( benzyloxycarbonyl A constant cumrnt ryi CDI co CHD 1.3 or 1.4-cyclohexadiene aa CHIRAPHOS 2.3-bis(diphenylphosphino)butane Chx(Cy) cyclohexyl O CIP CM (XMET) cross metathesis CMMP cyanomethylenetrimethyl phosphorane COD 1.5-cyclooctadiene O COT 1.3.5-cyclooctatriene O Cp @ CPTS collidinium-p-toluenesulfonate 013p t
TABLE OF CONTENTS SEARCH TEXT xxi Abbreviation Chemical Name Chemical Structure ca circa (approximately) NA CA chloroacetyl O Cl CAN cerium(IV) ammonium nitrate (cericammonium nitrate) Ce(NH4)2(NO3)6 cat. catalytic NA CB catecholborane O HB O CBS Corey-Bakshi-Shibata reagent N B O H Ph Ph R R = H, alkyl Cbz (Z) benzyloxycarbonyl O O cc. or conc. concentrated NA CCE constant current electrolysis NA CDI carbonyl diimidazole O N N N N CHD 1,3 or 1,4-cyclohexadiene 1,3-CHD 1,4-CHD CHIRAPHOS 2,3-bis(diphenylphosphino)butane (S) P (S) Ph Ph P Ph Ph Chx (Cy) cyclohexyl CIP 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate N NH Cl PF6 CM (XMET) cross metathesis NA CMMP cyanomethylenetrimethyl phosphorane P N COD 1,5-cyclooctadiene COT 1,3,5-cyclooctatriene Cp cyclopentadienyl CPTS collidinium-p-toluenesulfonate S NH O O O
TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure CRA complex reducing agent NA Cr-PILC chromium-pillared clay catalyst NA CSA camphorsufonic acid 毛 chlorosulfonyl isocyanate 3 CTAB cetyl trimethylammonium bromide CTACI cetyl trimethylammonium chloride 8 CTAP cetyl trimethylammonium permanganate heat days (length of reaction time) NA DABCO 1.4-diazabicyclo[2.2.2]octane 0=必 DAST diethylaminosulfur trifluoride R DATMP diethylaluminum 2.6.6-tetramethylpiperidide 公 DBA(dba) dibenzylideneacetone DBAD di-tert-butylazodicarboxylate t3 DBI dibromoisocyanuric acid 兴
TABLE OF CONTENTS SEARCH TEXT xxii Abbreviation Chemical Name Chemical Structure CRA complex reducing agent NA Cr-PILC chromium-pillared clay catalyst NA CSA camphorsufonic acid O SO3H CSI chlorosulfonyl isocyanate Cl S O O N C O CTAB cetyl trimethylammonium bromide N Br CTACl cetyl trimethylammonium chloride N C15H31 Cl CTAP cetyl trimethylammonium permanganate N C15H31 MnO4 Δ heat NA d days (length of reaction time) NA DABCO 1,4-diazabicyclo[2.2.2]octane N N N N DAST diethylaminosulfur trifluoride S N F F F DATMP diethylaluminum 2,2,6,6-tetramethylpiperidide N AlEt2 DBA (dba) dibenzylideneacetone O Ph Ph DBAD di-tert-butylazodicarboxylate N NO O O O DBI dibromoisocyanuric acid N O N O NH r OB Br
TABLE OF CONTENTS SEARCHTEXT Abbreviation Chemical Name Chemical Structure DBM dibenzoylmethane ca DBN 1.5-diazabicyclo[4.3.0]non-5-ene 的 DBS dibenzosuberyl 03 DBU 1.8-diazabicyco[5.4.0]undec-7-ene 沁 DCA 9,10-dicyanoanthracene 中 DCB 1.2-dichlorobenzene 0 Dcc O DCE 1.1-dichloroethane DCM dichloromethane DCN 1.4-dicyanonaphthalene 0∞ Dcpm dicyclopropylmethyl AA DCU N.N'-dicyclohexylurea aAo DDQ 2.3-dichloro-5,6-dicyano-1.4-benzoquinone 实 de diastereomeric excess
TABLE OF CONTENTS SEARCH TEXT xxiii Abbreviation Chemical Name Chemical Structure DBM dibenzoylmethane O O DBN 1,5-diazabicyclo[4.3.0]non-5-ene N N 1 2 3 4 5 6 7 8 9 DBS dibenzosuberyl DBU 1,8-diazabicyclo[5.4.0]undec-7-ene N N 1 2 3 4 5 6 7 8 9 10 11 DCA 9,10-dicyanoanthracene CN CN DCB 1,2-dichlorobenzene Cl Cl DCC dicyclohexylcarbodiimide N C N DCE 1,1-dichloroethane Cl Cl DCM dichloromethane CH2Cl2 DCN 1,4-dicyanonaphthalene CN CN Dcpm dicyclopropylmethyl DCU N,N’-dicyclohexylurea N H O N H DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone O O NC NC Cl Cl de diastereomeric excess NA
SEANCH TEXT Abbreviation Chemical Name Chemical Structure DEAD diethyl azodicarboxylate 又 DEIPS DEPBT 0 DET diethyl tartrate DHP 3.4-dihydro-2H-pyran 0 DHQ dihydroquinine 2 (DHQ)2PHAL bis(dihydroquinino)phthalazine DHQD dihydroquinidine 柔 DHQD)PHAL is(dihydroquinidino)phthalazine 河 DIAD diisopropyl azodicarboxylate (diacetoxyiodo)benzene o
TABLE OF CONTENTS SEARCH TEXT xxiv Abbreviation Chemical Name Chemical Structure DEAD diethyl azodicarboxylate N N O O O O DEIPS diethylisopropylsilyl Si DEPBT 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin- 4(3H)-one N N N O O P OEt EtO O DET diethyl tartrate OH HO (R) (R) O O O O DHP 3,4-dihydro-2H-pyran O DHQ dihydroquinine N N H OH OMe H (DHQ)2PHAL bis(dihydroquinino)phthalazine N MeO N Et H O NN O N H Et H N OMe H DHQD dihydroquinidine N OMe H OH H N (DHQD)2PHAL bis(dihydroquinidino)phthalazine N OMe N H O N N O N H H N MeO H Et Et DIAD diisopropyl azodicarboxylate N N O O O O DIB (BAIB or PIDA) (diacetoxyiodo)benzene I O O O O
TABLE OF CONTENTS SEARCH TEXT Abbreviation Chemical Name Chemical Structure DBe。品RA disobutylaluminum hydride 人是人 DIC Y人 diop 4.5-bis-[(diphenylp m2-dmeuy- m DIPAMP 1.2-bis(o-anisylphenylphosphino)ethane (Hom) diisopropylethylamine 和 DIPT diisopropyl tartrate DLP dilauroyl peroxide c DMA (DMAC) N.N-dimethylacetamide DMAD dimethyl acetylene dicarboxylate &大 DMAP N.N-4-dimethylaminopyridine DMB m-dimethoxybenzene Q DMDO dimethyl dioxirane 8 DME 1,2-dimethoxyethane XXV
TABLE OF CONTENTS SEARCH TEXT xxv Abbreviation Chemical Name Chemical Structure DIBAL (DIBAH) DIBAL-H diisobutylaluminum hydride Al H DIC diisopropyl carbodiimide N C N diop 4,5-bis-[(diphenylphosphanyl)methyl]-2,2-dimethyl- [1,3]dioxolane (R) O (R) O PPh2 PPh2 DIPAMP 1,2-bis(o-anisylphenylphosphino)ethane P O P O DIPEA (Hünig's base) diisopropylethylamine N DIPT diisopropyl tartrate OH HO (R) (R) O O O O DLP dilauroyl peroxide O O C10H21 O C10H21 O DMA (DMAC) N,N-dimethylacetamide O N DMAD dimethyl acetylene dicarboxylate O O O O DMAP N,N-4-dimethylaminopyridine N N DMB m-dimethoxybenzene O O DMDO dimethyl dioxirane O O DME 1,2-dimethoxyethane O O
SEANCH TEXT Abbreviation Chemical Name Chemical Structure DMF N.N-dimethylformamide DMI 1.3-dimethylimidazolidin-one 8 DMP Dess-Martin periodinane 第 DMPS dimethylphenylsilyl 0 DMPU 1.3-dimethyl-3.4.5.6-tetrahydro-2(1H)-pyrimidone (N.N-dimethy propylene urea) X DMTSF dimethyl(methylthio)sulfonium tetrafluoroborate w DMS dimethylsulfide DMSO dimethylsulfoxide 且 0 DMT 4.4'-dimethoxytrityl DMTMM 446eimnM35mao22-4 0 DMTr 4.4'-dimethyltrityl a DMTST 肚 DNA deoxyribonucleic acid NA
TABLE OF CONTENTS SEARCH TEXT xxvi Abbreviation Chemical Name Chemical Structure DMF N,N-dimethylformamide O N H DMI 1,3-dimethylimidazolidin-2-one NN O DMP Dess-Martin periodinane I O O AcO OAc OAc DMPS dimethylphenylsilyl Si DMPU 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone (N,N-dimethyl propylene urea) N N O DMTSF dimethyl(methylthio)sulfonium tetrafluoroborate Me S S Me Me BF4 DMS dimethylsulfide S DMSO dimethylsulfoxide S O DMT 4,4’-dimethoxytrityl O O DMTMM 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4- methylmorpholinium chloride N O N N N O O Cl DMTr 4,4’-dimethyltrityl DMTST (dimethylthio)methylsulfonium trifluoromethanesulfonate S S S S O O O F F F DNA deoxyribonucleic acid NA