Organic Letters, ISSN 1523-7060, 08/2007, Volume 9, Issue 16, pp. 3001 - 3004
A synthesis of an amphidinolides G and H C3−C18 subunits is reported. The C10−C18 segment 4 was prepared by a Negishi cross-coupling, whereas the synthesis of...
SEGMENT | MOIETY | STEREOCHEMISTRY | DINOFLAGELLATE | CHEMISTRY, ORGANIC | CYTOTOXIC AGENTS AMPHIDINOLIDES | POLYKETIDES | ALDEHYDES | BIOACTIVE MACROLIDES | ALPHA-ALLENIC ACETATES | GENERAL-METHOD | Molecular Structure | Catalysis | Macrolides - chemistry | Macrolides - chemical synthesis
SEGMENT | MOIETY | STEREOCHEMISTRY | DINOFLAGELLATE | CHEMISTRY, ORGANIC | CYTOTOXIC AGENTS AMPHIDINOLIDES | POLYKETIDES | ALDEHYDES | BIOACTIVE MACROLIDES | ALPHA-ALLENIC ACETATES | GENERAL-METHOD | Molecular Structure | Catalysis | Macrolides - chemistry | Macrolides - chemical synthesis
Journal Article
2.
Amphidinolide C3, a new cytotoxic 25-membered macrolide from marine dinoflagellate Amphidinium sp
Heterocycles, ISSN 0385-5414, 2010, Volume 82, Issue 1, pp. 333 - 338
A new cytotoxic 25-membered macrolide, amphidinolide C3 (1), has been isolated from marine dinoflagellate Amphidinium sp. (Y-56 strain), and the structure of 1...
CARTERAE | TRUNCATED POLYHYDROXYL CHAIN | LUTEOPHANOL | Dinoflagellate | COMPOUND | CHEMISTRY, ORGANIC | ABSOLUTE STEREOCHEMISTRY | Macrolide | Amphidinium species | Amphidinolide C3 | KLEBSII | BIOACTIVE MACROLIDES | ANTIFUNGAL | LINGSHUIOL | METABOLITE
CARTERAE | TRUNCATED POLYHYDROXYL CHAIN | LUTEOPHANOL | Dinoflagellate | COMPOUND | CHEMISTRY, ORGANIC | ABSOLUTE STEREOCHEMISTRY | Macrolide | Amphidinium species | Amphidinolide C3 | KLEBSII | BIOACTIVE MACROLIDES | ANTIFUNGAL | LINGSHUIOL | METABOLITE
Journal Article
Tetrahedron Letters, ISSN 0040-4039, 01/2014, Volume 55, Issue 4, pp. 900 - 902
The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-1-ol, which gave the C3–C9 fragment of amphidinolide Y, was the...
Amphidinolides | Macrocyclizations | Formal total synthesis | Ring-closing metathesis (RCM) | ALCOHOLS | ACID | RING-CLOSING METATHESIS | ESTERS | CHEMISTRY, ORGANIC | EFFICIENT | Synthesis (chemistry) | Marine | Precursors | Tetrahedrons | Joining | Derivatives | Conversion | Fragmentation
Amphidinolides | Macrocyclizations | Formal total synthesis | Ring-closing metathesis (RCM) | ALCOHOLS | ACID | RING-CLOSING METATHESIS | ESTERS | CHEMISTRY, ORGANIC | EFFICIENT | Synthesis (chemistry) | Marine | Precursors | Tetrahedrons | Joining | Derivatives | Conversion | Fragmentation
Journal Article
Letters in Organic Chemistry, ISSN 1570-1786, 05/2006, Volume 3, Issue 5, pp. 390 - 395
Stereoselective synthesis of C1-C6 fragment of caribenolide 1, a potent antitumour macrolide isolated from a marine dinoflagellate Amphidinium sp. is...
Oxazolidinones | Antitumor | Oxazolidin-2-thiones | Amphidinolide | Macrolide | Aldolisation | Cytotoxic activity | antitumor | oxazolidin-2-thiones | ASYMMETRIC ALDOL ADDITIONS | DINOFLAGELLATE | CHEMISTRY, ORGANIC | aldolisation | cytotoxic activity | AMPHIDINIUM SP | oxazolidinones | amphidinolide | macrolide
Oxazolidinones | Antitumor | Oxazolidin-2-thiones | Amphidinolide | Macrolide | Aldolisation | Cytotoxic activity | antitumor | oxazolidin-2-thiones | ASYMMETRIC ALDOL ADDITIONS | DINOFLAGELLATE | CHEMISTRY, ORGANIC | aldolisation | cytotoxic activity | AMPHIDINIUM SP | oxazolidinones | amphidinolide | macrolide
Journal Article
Tetrahedron, ISSN 0040-4020, 03/2018, Volume 74, Issue 13, pp. 1546 - 1554
The C18–C26 fragment of amphidinolide C congeners has been synthesized starting from methyl acetoacetate in 14 steps in >17.0% overall yield. The C20...
Tetrahydrofuran | Asymmetric dihydroxylation | Amphidinolide C | Enyne | Intramolecular SN2 reaction | Sonogashira cross-coupling | Intramolecular S | 2 reaction
Tetrahydrofuran | Asymmetric dihydroxylation | Amphidinolide C | Enyne | Intramolecular SN2 reaction | Sonogashira cross-coupling | Intramolecular S | 2 reaction
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 06/2014, Volume 53, Issue 25, pp. 6393 - 6396
A sequence comprising a ring‐closing alkyne metathesis of a propargyl alcohol derivative, followed by a ruthenium‐catalyzed redox isomerization of the derived...
ruthenium | 1,4 additions | metathesis | alkynes | molybdenum | CLOSING ALKYNE METATHESIS | LYTHRACEOUS ALKALOIDS | LYTHRAMINE | ASYMMETRIC-SYNTHESIS | LYTHRANINE | FORMAL TOTAL-SYNTHESIS | CHEMISTRY, MULTIDISCIPLINARY | ALCOHOLS | CATALYZED REDOX ISOMERIZATION | LYTHRUM-ANCEPS MAKINO | AMPHIDINOLIDE-V | Alkaloids - chemical synthesis | Molecular Structure | Catalysis | Oxidation-Reduction | Ruthenium - chemistry | Alkaloids - chemistry | Alkaloids | Synthesis | Molybdenum | Isomerization | Organic compounds | Acetylene | Catalysts | Decomposition reactions | Metathesis | Derivatives | Alkynes
ruthenium | 1,4 additions | metathesis | alkynes | molybdenum | CLOSING ALKYNE METATHESIS | LYTHRACEOUS ALKALOIDS | LYTHRAMINE | ASYMMETRIC-SYNTHESIS | LYTHRANINE | FORMAL TOTAL-SYNTHESIS | CHEMISTRY, MULTIDISCIPLINARY | ALCOHOLS | CATALYZED REDOX ISOMERIZATION | LYTHRUM-ANCEPS MAKINO | AMPHIDINOLIDE-V | Alkaloids - chemical synthesis | Molecular Structure | Catalysis | Oxidation-Reduction | Ruthenium - chemistry | Alkaloids - chemistry | Alkaloids | Synthesis | Molybdenum | Isomerization | Organic compounds | Acetylene | Catalysts | Decomposition reactions | Metathesis | Derivatives | Alkynes
Journal Article
Tetrahedron, ISSN 0040-4020, 2009, Volume 65, Issue 34, pp. 6828 - 6833
A new strategy for enantioselective assembly of the trisubstituted tetrahydrofuran ring has been established for synthesis of the C1–C12 acid fragment of...
γ-Butyrolactone | Samarium | Amphidinolide | Macrolide | Allylation
γ-Butyrolactone | Samarium | Amphidinolide | Macrolide | Allylation
Journal Article
Angewandte Chemie International Edition, ISSN 1433-7851, 01/2011, Volume 50, Issue 1, pp. 304 - 309
Out of options? Even though a systematic approach was chosen, which led to a set of four diastereomeric macrolides modeled around the proposed structure of...
marine natural products | structure elucidation | total synthesis | NMR spectroscopy | Homogeneous catalysis | ACIDS | NATURAL-PRODUCTS | AQUEOUS HYDROGEN-PEROXIDE | CATALYZED ASYMMETRIC EPOXIDATION | MACROLIDES | CHEMISTRY, MULTIDISCIPLINARY | ALCOHOLS | CROSS-COUPLING REACTIONS | AMPHIDINOLIDE-X | STRUCTURE REVISION | Marine Biology | Biological Products - chemistry | Oxazoles - metabolism | Macrolides - chemistry | Magnetic Resonance Spectroscopy | Oxazoles - analysis | Biological Products - metabolism | Biological Products - analysis | Macrolides - analysis | Molecular Structure | Macrolides - metabolism | Oxazoles - chemistry
marine natural products | structure elucidation | total synthesis | NMR spectroscopy | Homogeneous catalysis | ACIDS | NATURAL-PRODUCTS | AQUEOUS HYDROGEN-PEROXIDE | CATALYZED ASYMMETRIC EPOXIDATION | MACROLIDES | CHEMISTRY, MULTIDISCIPLINARY | ALCOHOLS | CROSS-COUPLING REACTIONS | AMPHIDINOLIDE-X | STRUCTURE REVISION | Marine Biology | Biological Products - chemistry | Oxazoles - metabolism | Macrolides - chemistry | Magnetic Resonance Spectroscopy | Oxazoles - analysis | Biological Products - metabolism | Biological Products - analysis | Macrolides - analysis | Molecular Structure | Macrolides - metabolism | Oxazoles - chemistry
Journal Article
Helvetica Chimica Acta, ISSN 0018-019X, 07/2019, Volume 102, Issue 7, p. n/a
In this article, we report the rapid and facile synthesis of chiral 3‐methyl‐2,5‐trans‐tetrahydrofurans. This reaction utilizes cheap and easily available...
gram-scale syntheses | diastereoselectivity | 3-methyl-2,5-trans-tetrahydrofurans | synthetic methods | ring closure | FORMAL SYNTHESIS | AMPHIDINOLIDES C | (-)-GYMNODIMINE | CHEMISTRY, MULTIDISCIPLINARY | 5-trans-tetrahydrofurans | BIOACTIVE MACROLIDES | 3-methyl-2 | ENANTIOSELECTIVE TOTAL-SYNTHESIS | C1-C9 FRAGMENT | Hydrolysis | Chemical synthesis | Furans | Stereoselectivity | Organic chemistry
gram-scale syntheses | diastereoselectivity | 3-methyl-2,5-trans-tetrahydrofurans | synthetic methods | ring closure | FORMAL SYNTHESIS | AMPHIDINOLIDES C | (-)-GYMNODIMINE | CHEMISTRY, MULTIDISCIPLINARY | 5-trans-tetrahydrofurans | BIOACTIVE MACROLIDES | 3-methyl-2 | ENANTIOSELECTIVE TOTAL-SYNTHESIS | C1-C9 FRAGMENT | Hydrolysis | Chemical synthesis | Furans | Stereoselectivity | Organic chemistry
Journal Article
Asian Journal of Organic Chemistry, ISSN 2193-5807, 03/2018, Volume 7, Issue 3, pp. 490 - 508
The Pd‐catalyzed, CuI−carboxylate‐mediated cross‐coupling reaction of organosulfur compounds with nucleophilic organometallic reagents is known as the...
cross-coupling | copper | palladium | synthetic methods | organosulfur reagents | ROOM-TEMPERATURE | HYDROGEN SUBSTITUTION-REACTIONS | EFFICIENT SYNTHESIS | CHEMISTRY, ORGANIC | THIOL ESTERS | LIGHT-HARVESTING ARRAYS | CARBON BOND FORMATION | BORONIC ACIDS | AMPHIDINOLIDE-C | TRANSITION-METAL | ASYMMETRIC AUTOCATALYSIS
cross-coupling | copper | palladium | synthetic methods | organosulfur reagents | ROOM-TEMPERATURE | HYDROGEN SUBSTITUTION-REACTIONS | EFFICIENT SYNTHESIS | CHEMISTRY, ORGANIC | THIOL ESTERS | LIGHT-HARVESTING ARRAYS | CARBON BOND FORMATION | BORONIC ACIDS | AMPHIDINOLIDE-C | TRANSITION-METAL | ASYMMETRIC AUTOCATALYSIS
Journal Article
Natural Product Reports, ISSN 0265-0568, 2009, Volume 26, Issue 2, pp. 245 - 265
An overview of marine natural products synthesis during 2007 is provided. As with earlier installments in this series, the emphasis is on total syntheses of...
CHEMISTRY, MEDICINAL | ASYMMETRIC-SYNTHESIS | 14-MEMBERED DIENE UNIT | BIOCHEMISTRY & MOLECULAR BIOLOGY | METHYL SARCOPHYTOATE | CHEMISTRY, ORGANIC | ABSOLUTE-CONFIGURATION | 1ST TOTAL-SYNTHESIS | AMPHIDINOLIDE-Y | HISTONE DEACETYLASE INHIBITORS | 6-PI-2-AZATRIENE ELECTROCYCLIZATION | ENANTIOSELECTIVE TOTAL-SYNTHESIS | PALMEROLIDE-A
CHEMISTRY, MEDICINAL | ASYMMETRIC-SYNTHESIS | 14-MEMBERED DIENE UNIT | BIOCHEMISTRY & MOLECULAR BIOLOGY | METHYL SARCOPHYTOATE | CHEMISTRY, ORGANIC | ABSOLUTE-CONFIGURATION | 1ST TOTAL-SYNTHESIS | AMPHIDINOLIDE-Y | HISTONE DEACETYLASE INHIBITORS | 6-PI-2-AZATRIENE ELECTROCYCLIZATION | ENANTIOSELECTIVE TOTAL-SYNTHESIS | PALMEROLIDE-A
Journal Article
Molecules, ISSN 1420-3049, 07/2011, Volume 16, Issue 7, pp. 5422 - 5436
beta-Hydroxy aldehyde and alkyl ketone moieties were effectively synthesized as key intermediates of amphidinolide Q, a cytotoxic macrolide from the cultured...
Macrolide synthesis | Amphidinolide Q | Cytotoxic marine natural product | Amphidinium sp | CHEMISTRY, ORGANIC | amphidinolide Q | macrolide synthesis | cytotoxic marine natural product | Ascorbic Acid | Macrolides - chemistry | Magnetic Resonance Spectroscopy | Macrolides - chemical synthesis | Stereoisomerism | Molecular Structure | Dinoflagellida - chemistry
Macrolide synthesis | Amphidinolide Q | Cytotoxic marine natural product | Amphidinium sp | CHEMISTRY, ORGANIC | amphidinolide Q | macrolide synthesis | cytotoxic marine natural product | Ascorbic Acid | Macrolides - chemistry | Magnetic Resonance Spectroscopy | Macrolides - chemical synthesis | Stereoisomerism | Molecular Structure | Dinoflagellida - chemistry
Journal Article
Tetrahedron, ISSN 0040-4020, 2007, Volume 63, Issue 26, pp. 5768 - 5796
Four amphidinolide E stereoisomers, amphidinolide E ( ), 2- -amphidinolide E ( ), 19- -amphidinolide E ( ), and 2- -19- -amphidinolide E ( ), have been...
[3+2] Annulation reaction | Esterification of Fe(CO) 3-complexed dienoic acid | Amphidinolide E stereoisomers | Esterification of Fe(CO) | complexed dienoic acid | TETRAHYDROFURAN SYNTHESIS | CHEMISTRY, ORGANIC | CHIRAL ALLYLSILANES | [3+2] annulation reaction | amphidinolide E stereoisomers | 3+2 ANNULATION | RING-CLOSING METATHESIS | DIASTEREOSELECTIVE SYNTHESIS | CHLOROSULFONYL ISOCYANATE | STEREOSELECTIVE-SYNTHESIS | esterification of Fe(CO)-complexed dienoic acid | ENANTIOSELECTIVE TOTAL-SYNTHESIS | CATALYTIC ASYMMETRIC-SYNTHESIS | MARINE POLYHYDROXYLATED STEROIDS | Chemical synthesis | Carbonyl compounds | Chemical reactions | esterification of Fe(CO)3-complexed dienoic acid
[3+2] Annulation reaction | Esterification of Fe(CO) 3-complexed dienoic acid | Amphidinolide E stereoisomers | Esterification of Fe(CO) | complexed dienoic acid | TETRAHYDROFURAN SYNTHESIS | CHEMISTRY, ORGANIC | CHIRAL ALLYLSILANES | [3+2] annulation reaction | amphidinolide E stereoisomers | 3+2 ANNULATION | RING-CLOSING METATHESIS | DIASTEREOSELECTIVE SYNTHESIS | CHLOROSULFONYL ISOCYANATE | STEREOSELECTIVE-SYNTHESIS | esterification of Fe(CO)-complexed dienoic acid | ENANTIOSELECTIVE TOTAL-SYNTHESIS | CATALYTIC ASYMMETRIC-SYNTHESIS | MARINE POLYHYDROXYLATED STEROIDS | Chemical synthesis | Carbonyl compounds | Chemical reactions | esterification of Fe(CO)3-complexed dienoic acid
Journal Article
08/2009, Volume 2009, Issue 23, 13
Complexation of (tricarbonyl)iron to an acyclic diene serves to protect the ligand against oxidation, reduction, and cycloaddition reactions, whereas the...
Iron | Synthetic methods | Regioselectivity | Diene ligands | Nucleophilic addition | MACROLACTIN-A | ORGANOIRON METHODOLOGY | ASYMMETRIC-SYNTHESIS | ENANTIOSELECTIVE SYNTHESIS | TRICARBONYLIRON COMPLEXES | CHEMISTRY, ORGANIC | ABSOLUTE STEREOCHEMISTRY | AMPHIDINOLIDE-E | FREE-RADICAL CYCLIZATIONS | (3-METHYLPENTADIENYL)IRON(1+) CATIONS | HIGHLY STEREOSELECTIVE-SYNTHESIS | Regioselective nucleophilic addition
Iron | Synthetic methods | Regioselectivity | Diene ligands | Nucleophilic addition | MACROLACTIN-A | ORGANOIRON METHODOLOGY | ASYMMETRIC-SYNTHESIS | ENANTIOSELECTIVE SYNTHESIS | TRICARBONYLIRON COMPLEXES | CHEMISTRY, ORGANIC | ABSOLUTE STEREOCHEMISTRY | AMPHIDINOLIDE-E | FREE-RADICAL CYCLIZATIONS | (3-METHYLPENTADIENYL)IRON(1+) CATIONS | HIGHLY STEREOSELECTIVE-SYNTHESIS | Regioselective nucleophilic addition
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