Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations

scientific article published on 13 May 2014

Synthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations is …
instance of (P31):
scholarly articleQ13442814

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P356DOI10.1002/ANIE.201403006
P932PMC publication ID4126560
P698PubMed publication ID24825410

P2093author name stringYu Bai
Mingji Dai
Dexter C Davis
P2860cites workFormal synthesis of (-)-kendomycin featuring a Prins-cyclization to construct the macrocycleQ24644824
Total Synthesis of (−)-Callipeltoside AQ30498592
Activation of thiol esters. Partial synthesis of cytochalasins A and BQ67656670
Synthesis of leucascandrolide A via a spontaneous macrolactolizationQ78512892
Lyngbyaloside B, a new glycoside macrolide from a Palauan marine cyanobacterium, Lyngbya spQ78718908
Diversity-oriented synthesis of fused pyran gamma-lactones via an efficient Pd-thiourea-catalyzed alkoxycarbonylative annulationQ79609766
Neopeltolide, a macrolide from a lithistid sponge of the family NeopeltidaeQ79797148
Formal total synthesis of (-)-apicularen A via transannular conjugate additionQ79889394
Two-faced reactivity of alkenes: cis- versus trans-aminopalladation in aerobic Pd-catalyzed intramolecular aza-Wacker reactionsQ80169789
Synthesis of large ring macrocycles (12-18) by recyclable palladium-complexed dendrimers on silica gel catalyzed intramolecular cyclocarbonylation reactionsQ80182413
Formal total synthesis of neopeltolideQ80779180
Total synthesis of (+)-neopeltolide by a Prins macrocyclizationQ80891441
Sequence of intramolecular carbonylation and asymmetric hydrogenation reactions: highly regio- and enantioselective synthesis of medium ring tricyclic lactamsQ81179630
Total synthesis of cyanolide AQ82859488
Synthesis of the macrolactone core of (+)-neopeltolide by transannular cyclizationQ83794079
Stereoselective synthesis of the macrolactone core of (+)-neopeltolideQ83929197
Diastereoselective total synthesis of (±)-schindilactone AQ84523768
Concise formal synthesis of (+)-neopeltolideQ85088563
A facile one-pot synthesis of a new cryptand via a Pd(II)-catalysed carbonylation reactionQ85105997
A Combinatorial Synthesis of a Macrosphelide Library Utilizing a Palladium‐Catalyzed Carbonylation on a Polymer SupportQ33194590
Total synthesis and stereochemical reassignment of (+)-neopeltolideQ33306228
Efficient synthetic access to a new family of highly potent bryostatin analogues via a Prins-driven macrocyclization strategyQ33331435
Total synthesis of neopeltolide and analogsQ34048909
A diversity-oriented synthesis approach to macrocycles via oxidative ring expansionQ34190644
Concise synthesis and biological assessment of (+)-neopeltolide and a 16-member stereoisomer library of 8,9-dehydroneopeltolide: identification of pharmacophoric elementsQ34680342
Synthesis and biological evaluation of neopeltolide and analogsQ35841039
Dual macrolactonization/pyran-hemiketal formation via acylketenes: applications to the synthesis of (-)-callipeltoside A and a lyngbyaloside B model systemQ36128295
Macrolactonizations in the total synthesis of natural productsQ36415708
The exploration of macrocycles for drug discovery--an underexploited structural classQ37203934
Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycleQ37348332
Update 1 of: macrolactonizations in the total synthesis of natural productsQ38045958
Synthesis of heterocycles via palladium-catalyzed carbonylationsQ38049601
Tetrahydrofuran-containing macrolides: a fascinating gift from the deep sea.Q38090647
Enantioselective synthesis of (-)-exiguolide by iterative stereoselective dioxinone-directed Prins cyclizationsQ39471184
Total synthesis of aspergillide A and B based on the transannular oxy-Michael reactionQ39582416
Total synthesis and biological evaluation of (+)-neopeltolide and its analoguesQ39780479
Total synthesis of the antiproliferative macrolide (+)-neopeltolide.Q39796133
Total synthesis and structure-activity investigation of the marine natural product neopeltolideQ39815422
Total synthesis and biological activity of neopeltolide and analoguesQ39922234
Synthesis enables identification of the cellular target of leucascandrolide A and neopeltolideQ39976525
Total synthesis and structural revision of callipeltoside C.Q41554909
Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladationQ42000504
Formal synthesis of (-)-neopeltolide featuring a highly stereoselective oxocarbenium formation/reduction sequence.Q43054939
Palladium-catalyzed synthesis of tetrahydrofurans from gamma-hydroxy terminal alkenes: scope, limitations, and stereoselectivityQ43108185
Deuterium-labeling studies establishing stereochemistry at the oxypalladation step in Wacker-type oxidative cyclization of an o-allylphenolQ44793807
A palladium-catalyzed carbonylation approach to acid chloride synthesisQ45394879
Multicatalytic synthesis of alpha-pyrrolidinyl ketones via a tandem palladium(II)/indium(III)-catalyzed aminochlorocarbonylation/Friedel-Crafts acylation reactionQ46125339
Total synthesis of the marine macrolide (+)-neopeltolideQ46335728
Intramolecular carbonylation reactions with recyclable palladium-complexed dendrimers on silica: synthesis of oxygen, nitrogen, or sulfur-containing medium ring fused heterocyclesQ46758671
Total synthesis and structural revision of the marine macrolide neopeltolideQ46831128
Concise enantioselective total synthesis of neopeltolide macrolactone highlighted by ether transfer.Q50746513
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
Enantioselective total synthesis of macrolide (+)-neopeltolide.Q54768234
Preparation of acyltetronic acids using t-butyl acetothioacetate: total synthesis of the fungal metabolites carolic, carlosic, and carlic acidsQ56954493
Total Synthesis and Biological Assessment of (−)-Exiguolide and AnaloguesQ57521127
A Concise Total Synthesis of (+)-NeopeltolideQ57521133
Total Synthesis of (+)-NeopeltolideQ57521155
Total Synthesis of Nominal Lyngbouilloside AglyconQ59478811
P433issue25
P407language of work or nameEnglishQ1860
P921main subjectpalladiumQ1089
P304page(s)6519-6522
P577publication date2014-05-13
P1433published inAngewandte Chemie International EditionQ62023953
P1476titleSynthesis of tetrahydropyran/tetrahydrofuran-containing macrolides by palladium-catalyzed alkoxycarbonylative macrolactonizations
P478volume53

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cites work (P2860)
Q42314827Catalytic Carbonylative Spirolactonization of Hydroxycyclopropanols
Q53091035Catalytic macrolactonizations for natural product synthesis.
Q26749672Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product
Q48125257Diastereoselective Synthesis of Highly Substituted Tetrahydrofurans by Pd-Catalyzed Tandem Oxidative Cyclization-Redox Relay Reactions Controlled by Intramolecular Hydrogen Bonding.
Q48332830Domino Ring Expansion: Regioselective Access to 9-Membered Lactones with a Fused Indole Unit from 2-Nitrophenyl-1,3-cyclohexanediones.
Q38311744Ester coupling reactions--an enduring challenge in the chemical synthesis of bioactive natural products
Q42654406Exo-selective reductive macrocyclization of ynals.
Q53300578Rapid synthesis of bicyclic lactones via palladium-catalyzed aminocarbonylative lactonizations.
Q50053664Recent Developments in Pd(0)-Catalyzed Alkene Carboheterofunctionalization Reactions
Q38835091Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs
Q85435784Total Synthesis and Structural Reassignment of Lyngbyaloside C Highlighted by Intermolecular Ketene Esterification
Q42320239Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization
Q91559361Total Synthesis of trans-Resorcylide via Macrocyclic Stille Carbonylation
Q93264600Total Synthesis, Biological Evaluation, and Target Identification of Rare Abies Sesquiterpenoids
Q48280289Total synthesis of (+)-herboxidiene/GEX 1A.

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