skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Total synthesis campaigns toward chlorophylls and related natural hydroporphyrins – diverse macrocycles, unrealized opportunities

Journal Article · · Natural Product Reports
DOI:https://doi.org/10.1039/C8NP00020D· OSTI ID:1439482

Quantitative evaluation of reported routes toward bonellin, chlorophyll a , and tolyporphin A suggests heuristics for practical syntheses of native hydroporphyrins.

Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
FG02-05ER15661
OSTI ID:
1439482
Journal Information:
Natural Product Reports, Journal Name: Natural Product Reports Vol. 35 Journal Issue: 9; ISSN 0265-0568
Publisher:
Royal Society of Chemistry (RSC)Copyright Statement
Country of Publication:
United Kingdom
Language:
English
Citation Metrics:
Cited by: 29 works
Citation information provided by
Web of Science

References (77)

Investigation of a Synthesis of meso-Porphyrins Employing High Concentration Conditions and an Electron Transport Chain for Aerobic Oxidation journal February 1994
The total synthesis of chlorophyll a journal January 1990
Total synthesis of (±)-bonellin dimethyl ester journal January 1983
Totalsynthese von (±)-Bonellin-dimethylester journal August 1991
The Condensation of Pyrroles with Bromine. A Self-Oxidation and a New Type of Displacement Reaction 1,2 journal July 1944
The structure of bonellin and its derivatives. Unique physiologically active chlorins from the marine echurian Bonellia viridis journal January 1980
Total Synthesis of the Proposed Structure of (+)-Tolyporphin AO,O-Diacetate journal April 1999
Teilsynthese von Methylphäophorbid a und Methylphäophorbid b journal January 1937
Partial syntheses of optically pure methyl bacteriopheophorbides c and d from methyl pheophorbide a journal May 1980
Quantitation of Tolyporphins, Diverse Tetrapyrrole Secondary Metabolites with Chlorophyll-Like Absorption, from a Filamentous Cyanobacterium-Microbial Community: Quantitation of Tolyporphins in a Cyanobacterium-Microbial Community journal November 2017
Synthetische Arbeiten auf dem Chlorophyllgebiet. Synthese des 2-Desäthyl-phylloporphyrins journal July 1952
The Preparation of Benzoylacetic Ester and some of its Homologs journal July 1932
De novo synthesis and photophysical characterization of annulated bacteriochlorins. Mimicking and extending the properties of bacteriochlorophylls journal January 2011
Revised Structure of Tolyporphin A journal April 1999
The total synthesis of chlorophyll journal January 1961
Novel Synthetic Routes to 8-Vinyl Chlorophyll Derivatives journal April 1998
Breakdown of Chlorophyll in Higher Plants-Phyllobilins as Abundant, Yet Hardly Visible Signs of Ripening, Senescence, and Cell Death journal February 2016
Hindered diffusion of porphyrins and short-chain polystyrene in small pores journal May 1989
Northern–Southern Route to Synthetic Bacteriochlorins journal November 2016
De Novo Synthesis of Stable Tetrahydroporphyrinic Macrocycles:  Bacteriochlorins and a Tetradehydrocorrin journal July 2005
Synthesis and photophysical characteristics of 2,3,12,13-tetraalkylbacteriochlorins journal January 2016
Discovery and Synthesis of Less Common Natural Hydroporphyrins journal March 1994
Totalsynthese des Chlorophylls journal September 1960
Modification of the Peripheral Substituents in Chlorophylls a and b and Their Derivatives (Review) journal April 2004
Synthesis of chlorins, bacteriochlorins and their tetraaza analogues journal July 2016
Metrics to ‘green’ chemistry—which are the best? journal January 2002
Vibrational Characteristics of Tetrapyrrolic Macrocycles journal October 1992
Laser desorption ionisation-time of flight mass spectrometry of the tolyporphins, bioactive metabolites from the cyanobacterium Tolypothrix nodosa journal February 2011
Synthese des Kopro- und Iso-Koproporphyrins journal January 1926
Partial synthesis of chlorophyll-a from rhodochlorin journal January 1981
Chemical transformations of bacteriochlorophyll a and its medical applications journal February 2016
De Novo Synthesis of Gem-Dialkyl Chlorophyll Analogues for Probing and Emulating Our Green World journal June 2015
Total Synthesis of (±)-Bonellin Dimethyl Ester journal September 1985
Synthesis of 24 Bacteriochlorin Isotopologues, Each Containing a Symmetrical Pair of 13 C or 15 N Atoms in the Inner Core of the Macrocycle journal January 2014
Chlorophyll a synthesis: A prefatory note journal January 1990
Tolyporphin, a novel multidrug resistance reversing agent from the blue-green alga Tolypothrix nodosa journal January 1992
The chemistry of pyrrolic compounds. XIX. Reactions of pyrrolic compounds with orthoformates journal January 1972
Neue Teilsynthesen von Methylphäophorbid a aus Chlorin e6-triester journal January 1941
Photophysical Characterization of the Naturally Occurring Dioxobacteriochlorin Tolyporphin A and Synthetic Oxobacteriochlorin Analogues journal July 2017
Synthesis and Structure of Tolyporphin A O,O -Diacetate journal October 1999
The Total Synthesis of Chlorophyll journal July 1960
The structure and physiological activity of bonellin - a unique chlorin derived from Bonellia viridis journal January 1979
Tolyporphins J and K, Two Further Porphinoid Metabolites from the Cyanobacterium Tolypothrix nodosa journal August 1998
Genome Sequence and Composition of a Tolyporphin-Producing Cyanobacterium-Microbial Community journal July 2017
Recent progress in chlorophyll and porphyrin chemistry journal January 1968
Biosynthesis of porphyrins and related macrocycles. Part VIII. Enzymic decarboxylation of uroporphyrinogen-III: structure of an intermediate, phyriaporphyrinogen-III, and synthesis of the corresponding porphyrin and of two isomeric porphyrins journal January 1976
Synthesis of the heme d prosthetic group of bacterial terminal oxidase journal March 1988
Chlorophyll Modifications and Their Spectral Extension in Oxygenic Photosynthesis journal June 2014
β-selective C-glycosidations: lewis-acid mediated reactions of carbohydrates with silyl ketene acetals journal September 1997
Chlorins: Natural Sources, Synthetic Developments and Main Applications journal April 2014
Carotenoids and related compounds. Part XIV. Stereochemistry and synthesis of geraniol, nerol, farnesol, and phytol journal January 1966
Rothemund and Adler-Longo reactions revisited: synthesis of tetraphenylporphyrins under equilibrium conditions journal March 1987
The Art and Science of Total Synthesis at the Dawn of the Twenty-First Century journal January 2000
Bacteriochlorophyll a and Its Derivatives: Chemistry and Perspectives for Cancer Therapy journal August 2008
Synthetic studies relevant to biosynthetic research on vitamin B 12 . Part 7. Synthesis of (±)-bonellin dimethyl ester journal January 1988
Synthetic Chlorins, Possible Surrogates for Chlorophylls, Prepared by Derivatization of Porphyrins journal March 2016
Construction of the Bacteriochlorin Macrocycle with Concomitant Nazarov Cyclization To Form the Annulated Isocyclic Ring: Analogues of Bacteriochlorophyll a journal February 2017
A stereocontrolled total synthesis of optically active (R,R)-phytol journal January 1981
Synthesis of Orthogonally Protected Pyrrole Tricarboxylic Acid Derivatives: Versatile Building Blocks for Pyrrole-Containing Compounds journal January 2006
How green is green chemistry? Chlorophylls as a bioresource from biorefineries and their commercial potential in medicine and photovoltaics journal January 2015
Recent Advances in the Synthesis of Hydroporphyrins journal October 2007
Zur weiteren Kenntnis des Chlorophylls und des Hämins, XXXII. Partialsynthese von Rhodin-g7-trimethylester aus Chlorin-e6-trimethylester, zugleich Vollendung der Harvard-Synthese des Chlorophylls a zum Chlorophyll b journal July 1971
Further tolyporphins from the Blue-Green alga Tolypothrix nodosa. journal September 1995
Mass spectrometric detection of chlorophyll a and the tetrapyrrole secondary metabolite tolyporphin A in the filamentous cyanobacterium HT-58-2. Approaches to high-throughput screening of intact cyanobacteria journal November 2017
Unification of Reaction Metrics for Green Chemistry:  Applications to Reaction Analysis journal March 2005
Synthese des 2.4-Dimethyl-5-carbäthoxy-3-vinyl-pyrrols und seine Überführung in Krypto-pyrrol journal December 1925
Structural Investigations upon a Substituted Dipyrrylmethane. An Unusual Melting Point-Symmetry Relationship 1,2 journal June 1942
Synthesis of Ethyne-Linked or Butadiyne-Linked Porphyrin Arrays Using Mild, Copper-Free, Pd-Mediated Coupling Reactions journal August 1995
Total Synthesis of Hematoporphyrin and Protoporphyrin: A Conceptually New Approach journal July 2010
Tetrapyrroles: the pigments of life journal January 2000
Tolyporphin Macrocycles from the Cyanobacterium Tolypothrix nodosa Selectively Bind Copper and Silver and Reverse Multidrug Resistance journal February 2017
A comprehensive review of glycosylated bacterial natural products journal January 2015
Synthesis of Bacteriochlorins and Their Potential Utility in Photodynamic Therapy (PDT) journal August 2004
Synthesis of the enantiomers of 4-substituted γ-lactones with known absolute configuration journal January 1978
The Breaking and Mending of meso -Tetraarylporphyrins: Transmuting the Pyrrolic Building Blocks journal March 2016
Expanded Scope of Synthetic Bacteriochlorins via Improved Acid Catalysis Conditions and Diverse Dihydrodipyrrin-Acetals journal February 2010
Spectroscopic and Crystallographic Investigations of Novel BODIPY-Derived Metal–Organic Frameworks journal January 2015