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Stereoselective Synthesis Of New Chlorophyll A Related Antioxidants Isolated From Marine Organisms

Lifu Ma, D. Dolphin
Published 1996 · Chemistry

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A new class of natural antioxidants, chlorophyll a related chlorins 3, 4(S), 4(R), 5(R), 6, 7, 8, and 9, have been synthesized from a chlorophyll a degradation product, pheophorbide a methyl ester (1). Claisen-type intramolecular condensation of pyropheophorbide a methyl ester (2) afforded the common intermediate enol 3. Chlorin 1 and enol 3 have a propensity to undergo exocyclic ring opening by ionic bases. The organic base DBU was found to be an efficient reagent for promoting the asymmetric hydroxylation of these chlorins, using N-sulfonyloxaziridines, without cleavage of the exocyclic rings. Model studies for hydroxylactonization have shown that periodate oxidation of hydroxy ketone 10 stereoselectively and predominantly forms hydroxy lactone 17(S). Periodate oxidation of α-hydroxy 1,3-diketone 4(R) and/or 4(S) to furnish hydroxy lactone 5(R) and diketone 7 was found out to be regioselective, and the site of reaction depends on the appropriate choice of reaction media. 1H NMR spectra have provided inf...



This paper is referenced by
10.1080/10826070701276515
Polystyrene‐Divinylbenzene (PS‐DVB), a Mild Stationary Phase for the Chromatographic Purification of the Unstable 132, 173‐Cyclopheophorbide a‐Enol
Mitra Mortezaei‐Rad (2007)
10.1002/9783527335855.MARPROD012
Chlorophyceae (Green Algae) and Marine Spermatophyta
J. Kornprobst (2014)
10.1002/cbdv.201000341
Derivatives of Pheophorbide‐a and Pheophorbide‐b from Photocytotoxic Piper penangense Extract
Fadzly Adzhar Kamarulzaman (2011)
10.1002/EJOC.201000940
A Simple and Effective Method for α-Hydroxylation of β-Dicarbonyl Compounds Using Oxone as an Oxidant without a Catalyst
Jun Yu (2010)
10.1039/c2cs35216h
BODIPY dyes in photodynamic therapy.
Anyanee Kamkaew (2013)
10.1248/CPB.55.343
New constituents from the leaves of Morinda citrifolia.
J. Takashima (2007)
10.1142/S1088424610002690
Synthesis of isoxazoline-linked chlorins and their in vitro cell viabilities
Jinjun Wang (2010)
10.1590/S0102-695X2008000500015
Constituintes químicos, avaliação das atividades citotóxica e antioxidante de Mimosa paraibana Barneby (Mimosaceae)
X. P. Nunes (2008)
10.1007/s10600-018-2364-5
Chemical Constituents of the Leaves of Michelia figo
H. C. Chen (2018)
10.1016/j.bmcl.2018.02.015
In vivo and in vitro preparation of divinyl-132,173-cyclopheophorbide-a enol.
Y. Kinoshita (2018)
10.1016/S0040-4020(00)00256-8
Syntheses and Spectroscopic Studies of Novel Chlorins with Fused Quinoxaline or Benzimidazole Ring Systems and the Related Dimers with Extended Conjugation
Andrei N. Kozyrev (2000)
10.1002/HLCA.200890125
Secondary metabolites from the stem bark of litsea akoensis and their cytotoxic activity
S. Chang (2008)
10.1016/J.JFF.2017.11.030
In vitro digestion of chlorophyll pigments from edible seaweeds
Kewei Chen (2018)
10.1007/s11120-007-9247-0
Self-aggregation behavior of synthetic zinc 3-hydroxymethyl-13/15-carbonyl-chlorins as models of main light-harvesting components in photosynthetic green bacteria
H. Tamiaki (2007)
10.1134/S1070363219090354
Chemical Transformations of Chlorophyll a and Possible Areas for Application of Its Derivatives
A. Mironov (2019)
10.1016/S0045-6535(03)00296-0
On the sedimentary occurrence of chlorophyllone a.
N. Aydin (2003)
10.1021/acs.joc.7b01831
Synthesis and Properties of Carbaporphyrin and Carbachlorin Dimethyl Esters Derived from Cyclopentanedialdehydes.
Navneet Sahota (2017)
10.1016/S0040-4039(97)00369-9
SYNTHESES AND SPECTROSCOPIC STUDIES OF SOME NOVEL PORPHYRIN-PYROPHEOPHORBIDE DIMERS AND TRIMERS WITH FIXED DISTANCES
G. Zheng (1997)
Mechanisms governing degradation of phytoplankton pigments in fjords
Susanne E. Schüller (2014)
10.1111/php.13319
Absorption and Fluorescence Spectral Database of Chlorophylls and Analogues.
M. Taniguchi (2020)
10.1007/s10600-014-1131-5
Secondary Metabolites from the Leaves of Victoria amazonica
M. Chang (2014)
10.1016/S0968-0896(01)00305-4
Antitumor agents. Part 209: Pheophorbide-a derivatives as photo-Independent cytotoxic agents.
P. Wongsinkongman (2002)
Tracing time in the ocean: Unraveling depositional and preservational timescales using compound-specific radiocarbon analysis of biomarkers from marine sediments
S. Kusch (2010)
10.1016/J.TETLET.2010.12.079
Hemisynthesis of 132,173-cyclomesopheophorbide-a-enol
Mitra Khalesi (2011)
10.1562/0031-8655(2001)073<0153:SSOSAS>2.0.CO;2
Supramolecular Structure of Self-assembled Synthetic Zinc-131-oxo-chlorins Possessing a Primary, Secondary or Tertiary Alcoholic 31-Hydroxyl Group: Visible Spectroscopic and Molecular Modeling Studies¶
S. Yagai (2001)
10.1016/S0304-4203(02)00138-X
Implications for the role of pre- versus post-depositional transformation of chlorophyll-a in the Lower Mississippi River and Louisiana shelf
Nianhong Chen (2003)
10.1039/B511314H
Mild and efficient method for the cleavage of benzylidene acetals by using erbium (III) triflate.
A. Procopio (2005)
10.1073/pnas.1207347109
Ubiquity and quantitative significance of detoxification catabolism of chlorophyll associated with protistan herbivory
Y. Kashiyama (2012)
10.1007/s10811-011-9698-8
Cyclic tetrapyrrolic photosensitizers from Cladophora patentiramea (Cladophoraceae, Chlorophyta) and Turbinaria conoides (Sargassaceae, Phaeophyta) for photodynamic therapy
Y. V. Tang (2011)
10.1016/S0146-6380(98)00104-1
Protected surface-enhanced resonance Raman spectroscopy for the study of geochemically significant chlorophyll transformation products
P. S. Woolley (1998)
10.1039/c8pp00173a
Ultrafast excited state dynamics of nonfluorescent cyclopheophorbide-a enol, a catabolite of chlorophyll-a detoxified in algae-feeding aquatic microbes.
Chikashi Ota (2019)
10.1016/J.TET.2006.01.043
The enolate anions of chlorophylls a and b as ambident nucleophiles in oxidations with (-)- or (+)-(10-camphorsulfonyl)oxaziridine. synthesis of 132(S/R)-hydroxychlorophylls a and b
P. Hynninen (2006)
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