Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis

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Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis is …
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P356DOI10.1021/JACS.6B02019
P932PMC publication ID4871165
P698PubMed publication ID27113543

P50authorMichael J. KrischeQ59588951
P2093author name stringZachary A Kasun
Jiajie Feng
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Natural products as sources of new drugs over the last 25 yearsQ29615119
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Total synthesis and stereochemical reassignment of (+)-neopeltolideQ33306228
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Total Synthesis of Bryostatin 3Q33913638
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Total synthesis of neopeltolide and analogsQ34048909
Total Synthesis of (+)-Roxaticin via C−C Bond Forming Transfer Hydrogenation: A Departure from Stoichiometric Chiral Reagents, Auxiliaries, and Premetalated Nucleophiles in Polyketide ConstructionQ34144693
Total synthesis of bryostatin 9Q34187866
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Analysis of the reactions used for the preparation of drug candidate moleculesQ34536453
Total synthesis of bryostatin 1Q34538229
Identification of the putative bryostatin polyketide synthase gene cluster from "Candidatus Endobugula sertula", the uncultivated microbial symbiont of the marine bryozoan Bugula neritinaQ34574375
Saliniketals A and B, bicyclic polyketides from the marine actinomycete Salinispora arenicolaQ34606298
An abiotic strategy for the enantioselective synthesis of erythromycin B.Q44522812
Synthesis of the antifungal macrolide antibiotic (+)-roxaticinQ44571457
Total synthesis of zincophorin and its methyl esterQ44961143
Two classes of metabolites from Theonella swinhoei are localized in distinct populations of bacterial symbionts.Q45954541
Total synthesis of the marine macrolide (+)-neopeltolideQ46335728
The asymmetric total synthesis of (+)-cytotrienin a, an ansamycin-type anticancer drugQ46469997
Total synthesis of 10-deoxymethynolide and narbonolideQ46801000
Total synthesis and structural revision of the marine macrolide neopeltolideQ46831128
Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the Red Sea sponge Theonella swinhoeiQ46914793
Total synthesis and stereochemical reassignment of mandelalide A.Q48863372
Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer.Q50746513
Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification.Q50914346
Total synthesis of (-)-reidispongiolide A, an actin-targeting marine macrolide.Q51705885
Total synthesis of the marine natural product (-)-clavosolide A.Q51724455
Total synthesis of the marine natural product (-)-clavosolide A. A showcase for the Petasis-Ferrier union/rearrangement tactic.Q51724460
Stereoselective synthesis of 2,6-trans-tetrahydropyran via primary diamine-catalyzed oxa-conjugate addition reaction of α,β-unsaturated ketone: total synthesis of psymberin.Q53402779
Stereoselective synthesis of 2,6-cis-tetrahydropyrans through a tandem allylic oxidation/oxa-Michael reaction promoted by the gem-disubstituent effect: synthesis of (+)-neopeltolide macrolactone.Q53497348
Catalytic carbonyl Z-dienylation via multicomponent reductive coupling of acetylene to aldehydes and alpha-ketoesters mediated by hydrogen: Carbonyl insertion into cationic rhodacyclopentadienes.Q53583133
Catalytic Enantioselective Addition of Allylic Organometallic Reagents to Aldehydes and KetonesQ56431040
A Concise Total Synthesis of (+)-NeopeltolideQ57521133
Total synthesis of zincophorinQ57776876
Total Synthesis of Zincophorin Methyl EsterQ57776884
Total Synthesis of (−)-Saliniketals A and B†Q58195191
Antineoplastic Components of Marine AnimalsQ59090309
Selectivity: A Key to Synthetic EfficiencyQ59405691
Total Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage SequenceQ59478361
Unlocking Hydrogenation for C-C Bond Formation: A Brief Overview of Enantioselective MethodsQ39372722
Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instabilityQ39405195
Total synthesis and biological evaluation of pederin, psymberin, and highly potent analogsQ39477338
Formal total synthesis of cyanolide A.Q39600353
1,n-glycols as dialdehyde equivalents in iridium-catalyzed enantioselective carbonyl allylation and iterative two-directional assembly of 1,3-polyolsQ39752033
Enantioselective carbonyl reverse prenylation from the alcohol or aldehyde oxidation level employing 1,1-dimethylallene as the prenyl donorQ39775784
Total synthesis of the antiproliferative macrolide (+)-neopeltolide.Q39796133
Total synthesis and structure-activity investigation of the marine natural product neopeltolideQ39815422
Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenationQ39837642
Total synthesis and biological activity of neopeltolide and analoguesQ39922234
A concise total synthesis of saliniketal BQ39950381
Synthesis enables identification of the cellular target of leucascandrolide A and neopeltolideQ39976525
Total synthesis and study of 6-deoxyerythronolide B by late-stage C-H oxidationQ40915450
Progress in the discovery of biosynthetic anticancer drugsQ41101985
Total Synthesis of Oridamycins A and B.Q41716938
Total synthesis of cyanolide A in the absence of protecting groups, chiral auxiliaries, or premetalated carbon nucleophilesQ41827256
Total synthesis of (+)-trienomycins A and F via C-C bond-forming hydrogenation and transfer hydrogenationQ41844095
Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolideQ41856494
Iridium-catalyzed allylation of chiral β-stereogenic alcohols: bypassing discrete formation of epimerizable aldehydesQ41880728
Direct Generation of Triketide Stereopolyads via Merged Redox-Construction Events: Total Synthesis of (+)-Zincophorin Methyl EsterQ42176919
Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyransQ42205765
Redox-triggered C-C coupling of alcohols and vinyl epoxides: diastereo- and enantioselective formation of all-carbon quaternary centers via tert-(hydroxy)-prenylationQ42255464
Chiral-anion-dependent inversion of diastereo- and enantioselectivity in carbonyl crotylation via ruthenium-catalyzed butadiene hydrohydroxyalkylationQ42431190
Formal Synthesis of Premisakinolide A and C(19)-C(32) of Swinholide A via Site-Selective C-H Allylation and Crotylation of Unprotected DiolsQ42591850
Cryptocaryols A and B: total syntheses, stereochemical revision, structure elucidation, and structure-activity relationshipQ42613219
ESI-MS, DFT, and synthetic studies on the H(2)-mediated coupling of acetylene: insertion of C=X bonds into rhodacyclopentadienes and Brønsted acid cocatalyzed hydrogenolysis of organorhodium intermediatesQ42675078
Enhanced anti-diastereo- and enantioselectivity in alcohol-mediated carbonyl crotylation using an isolable single component iridium catalystQ42704133
Protecting-group-free diastereoselective C-C coupling of 1,3-glycols and allyl acetate through site-selective primary alcohol dehydrogenationQ42724067
Elongation of 1,3-polyols via iterative catalyst-directed carbonyl allylation from the alcohol oxidation levelQ42731624
Diastereo- and enantioselective ruthenium-catalyzed hydrohydroxyalkylation of 2-silyl-butadienes: carbonyl syn-crotylation from the alcohol oxidation levelQ42789846
Swinholide J, a potent cytotoxin from the marine sponge Theonella swinhoeiQ42790041
Direct generation of acyclic polypropionate stereopolyads via double diastereo- and enantioselective iridium-catalyzed crotylation of 1,3-diols: beyond stepwise carbonyl addition in polyketide constructionQ42864646
Formal synthesis of (-)-neopeltolide featuring a highly stereoselective oxocarbenium formation/reduction sequence.Q43054939
Total synthesis of cyanolide A and confirmation of its absolute configuration.Q43057393
Concise synthesis of the bryostatin A-ring via consecutive C-C bond forming transfer hydrogenationsQ43068920
Ruthenium Catalyzed Diastereo- and Enantioselective Coupling of Propargyl Ethers with Alcohols: Siloxy-Crotylation via Hydride Shift Enabled Conversion of Alkynes to π-AllylsQ43119768
Catalytic asymmetric synthesis of complex polypropionates: Lewis base catalyzed aldol equivalents in the synthesis of erythronolide B.Q43139895
Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studiesQ43259132
Total synthesis of (+)-phorboxazole A exploiting the Petasis-Ferrier rearrangementQ43784759
Formal Total Synthesis of (-)-SaliniketalsQ44103224
[3 + 2] Annulation of allylic silanes in acyclic stereocontrol: total synthesis of (9S)-dihydroerythronolide A.Q44465179
Marine natural products. XXIII. Three new cytotoxic dimeric macrolides, swinholides B and C and isoswinholide A, congeners of swinholide A, from the Okinawan marine sponge Theonella swinhoeiQ34623671
Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level using allyl acetate as an allyl metal surrogateQ34774734
Enantioselective iridium-catalyzed carbonyl allylation from the alcohol or aldehyde oxidation level via transfer hydrogenative coupling of allyl acetate: departure from chirally modified allyl metal reagents in carbonyl additionQ34848081
Toward more "ideal" polyketide natural product synthesis: a step-economical synthesis of zincophorin methyl esterQ34975658
Total synthesis of the cyanolide A aglyconQ35097674
Total synthesis and antiviral activity of indolosesquiterpenoids from the xiamycin and oridamycin familiesQ35139432
Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition ReactionQ35898889
Enantioselective C-H crotylation of primary alcohols via hydrohydroxyalkylation of butadieneQ36226256
Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide AQ36494329
Griseochelin, a novel carboxylic acid antibiotic from Streptomyces griseus.Q36605286
Biological profile of the less lipophilic and synthetically more accessible bryostatin 7 closely resembles that of bryostatin 1.Q36781257
Total synthesis of (+)-irciniastatin A (a.k.a. psymberin) and (-)-irciniastatin BQ36836009
Formal synthesis of 6-deoxyerythronolide B.Q36897724
Asymmetric catalysis mediated by synthetic peptides.Q37029347
Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycleQ37348332
Total synthesis of (+)-psymberin (irciniastatin A): catalytic reagent control as the strategic cornerstoneQ37361293
Total synthesis of irciniastatin A (Psymberin).Q37364475
Redox economy in organic synthesisQ37417218
Impact of natural products on developing new anti-cancer agentsQ37473373
Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiencyQ37660116
Protecting-group-free synthesis as an opportunity for inventionQ37850298
The importance of green chemistry in process research and developmentQ37874451
Fundamentals of green chemistry: efficiency in reaction designQ37950243
From micrograms to grams: scale-up synthesis of eribulin mesylateQ38125086
Polyketide construction via hydrohydroxyalkylation and related alcohol C-H functionalizations: reinventing the chemistry of carbonyl additionQ38186988
Catalyst-directed diastereoselectivity in hydrogenative couplings of acetylene to alpha-chiral aldehydes: formal synthesis of all eight L-hexosesQ38280684
anti-Diastereo- and enantioselective carbonyl crotylation from the alcohol or aldehyde oxidation level employing a cyclometallated iridium catalyst: alpha-methyl allyl acetate as a surrogate to preformed crotylmetal reagentsQ38280705
Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A.Q38497852
Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl AdditionQ38549564
Enantioselective Total Synthesis of Mandelalide A and Isomandelalide A: Discovery of a Cytotoxic Ring-Expanded IsomerQ38804229
Total Synthesis and Biological Assessment of Mandelalide A.Q38814133
Total Synthesis and Biological Evaluation of Irciniastatin A (a.k.a. Psymberin) and Irciniastatin B.Q38821589
Total synthesis of dixiamycin B by electrochemical oxidationQ39044539
Isoswinholide B and swinholide K, potently cytotoxic dimeric macrolides from Theonella swinhoei.Q39129764
Toxins from cyanophytes belonging to the scytonemataceaeQ104155404
Marine natural products. XXII. The absolute stereostructure of swinholide A, a potent cytotoxic dimeric macrolide from the Okinawa marine sponge Theonella swinhoei.Q105237835
[Griseochelin methyl ester, a new polyether derivative with antiviral activity]Q68006707
Tolytoxin and new scytophycins from three species of ScytonemaQ68382317
Polyene macrolide antibiotic amphotericin B. Crystal structure of the N-iodoacetyl derivativeQ70630922
The structure and absolute stereochemistry of zincophorin (antibiotic M144255): a monobasic carboxylic acid ionophore having a remarkable specificity for divalent cationsQ70817564
A New Role for PolyketidesQ73068210
Total synthesis of (+)-thiazinotrienomycin EQ73823413
Total synthesis of the ansamycin antibiotic (+)-thiazinotrienomycin EQ73919271
Total Synthesis of Scytophycin CQ74835399
Isolation of Calyculins, Calyculinamides, and Swinholide H from the New Zealand Deep-Water Marine Sponge Lamellomorpha strongylataQ74836046
Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin IQ74837229
Total synthesis of scytophycin C. 1. Stereoselective syntheses of the C(1)-C(18) segment and the C(19)-C(31) segmentQ79079701
Total synthesis of scytophycin C. 2. Coupling reaction of the C(1)-C(18) segment and the C(19)-C(31) segment, a key macrolactonization, and the crucial terminal amidation reactionQ79079703
A formal synthesis of psymberinQ79824940
Creation of quaternary stereocenters in carbonyl allylation reactionsQ80212621
Enantioselective formal total synthesis of the antitumor macrolide bryostatin 7Q80302088
Enantioselective reductive coupling of acetylene to N-arylsulfonyl imines via rhodium catalyzed C-C bond-forming hydrogenation: (Z)-dienyl allylic aminesQ80354280
The total synthesis of psymberinQ80378812
Stereoselective total synthesis of the ionophore antibiotic zincophorinQ80565467
Formal total synthesis of neopeltolideQ80779180
Total synthesis of (+)-neopeltolide by a Prins macrocyclizationQ80891441
Synthesis and complete stereochemical assignment of psymberin/irciniastatin AQ81027612
Isolation of swinholide A and related glycosylated derivatives from two field collections of marine cyanobacteriaQ81567919
Stereoselective synthesis of premisakinolide A, the monomeric counterpart of the marine 40-membered dimeric macrolide misakinolide AQ81907248
Total synthesis, structural revision, and absolute configuration of (-)-clavosolide [corrected] AQ82513987
Enantioselective reductive coupling of alkynes and alpha-keto aldehydes via rhodium-catalyzed hydrogenation: an approach to bryostatin substructuresQ82631703
Syntheses and biological evaluation of irciniastatin A and the C1-C2 alkyne analogueQ82826538
Total synthesis of cyanolide AQ82859488
Chiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-.beta.-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranesQ82992216
Synthesis of molluscicidal agent cyanolide a macrolactone from D-(-)-pantolactoneQ83066314
An efficient formal synthesis of (-)-clavosolide a featuring a "mismatched" stereoselective oxocarbenium reductionQ83151467
Diastereo- and enantioselective iridium-catalyzed carbonyl propargylation from the alcohol or aldehyde oxidation level: 1,3-enynes as allenylmetal equivalentsQ83454484
Organic synthesis involving iridium-catalyzed oxidationQ83579500
Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclizationQ83794079
Stereoselective synthesis of the macrolactone core of (+)-neopeltolideQ83929197
Enantioselective carbonyl propargylation by iridium-catalyzed transfer hydrogenative coupling of alcohols and propargyl chloridesQ84465953
A formal synthesis of (-)-cyanolide A featuring a stereoselective Mukaiyama aldol reaction and oxocarbenium reductionQ84816110
Catalytic enantioselective allylation of carbonyl compounds and iminesQ84954385
Concise formal synthesis of (+)-neopeltolideQ85088563
The total synthesis of (-)-cryptocaryol AQ86770669
Formal total synthesis of (+)-neopeltolideQ87413003
Catalysis-based total synthesis of putative mandelalide AQ87431851
Asymmetric Synthesis of Bryostatin 2Q88519157
Chemoselectivity and stereoselectivity have been key factors in the development of fine organic synthesis. IntroductionQ95377276
Ilotycin, a new antibioticQ95545076
P433issue17
P407language of work or nameEnglishQ1860
P921main subjectenantioselectivityQ1339952
P304page(s)5467-5478
P577publication date2016-04-26
P1433published inJournal of the American Chemical SocietyQ898902
P1476titleEnantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis
P478volume138

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