Asymmetric synthesis of orsellinic acid type macrolides: The example of lasiodiplodin

Solladié, Guy; Rubio, Alberto Pérez; Carreño, M. Carmen; Ruano, JoséL. García

doi:10.1016/0957-4166(90)90013-z

Cited by 66 publications

(40 citation statements)

References 11 publications

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“…The latter can be easily transformed into lasiodiplodin and its demethylated congener, [17,20] which are natural products possessing anti-leukemic and prostaglandin-inhibitor activities, respectively. The latter can be easily transformed into lasiodiplodin and its demethylated congener, [17,20] which are natural products possessing anti-leukemic and prostaglandin-inhibitor activities, respectively.…”

Section: Discussionmentioning

confidence: 99%

“…[8,9] Another member of this family is lasiodiplodin, which displays antileukemia activity, [10] and its demethylated congener, which efficiently inhibits prostaglandin biosynthesis. [20] The first catalytic asymmetric synthesis, reported by Jones and Huber, was based on Cr-catalyzed enantioselective addition of Me 2 Zn onto an aldehyde (86 % ee). [20] The first catalytic asymmetric synthesis, reported by Jones and Huber, was based on Cr-catalyzed enantioselective addition of Me 2 Zn onto an aldehyde (86 % ee).…”

Section: Introductionmentioning

confidence: 99%

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Chemoenzymatic Asymmetric Total Synthesis of (R)‐Lasiodiplodin Methyl Ether through a Sulfatase‐Based Deracemization Process

et al. 2012

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(R)‐Lasiodiplodin methyl ether, a precursor of the antileukemic agent lasiodiplodin, was synthesized through a seven‐step linear sequence. Chirality was introduced through a sulfatase‐based deracemization process, in which a functionalized (rac)‐sec‐sulfate ester was enzymatically hydrolyzed with inversion of the stereocenter using an alkyl sulfatase. The remaining sulfate ester enantiomer was hydrolyzed with retention of configuration under acidic conditions, yielding the chiral key building block as the sole product in 93 % ee The total synthesis was completed through Negishi cross‐coupling and ring‐closing metathesis.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Asymmetric Total Synthesis of (R)‐Lasiodiplodin Methyl Ether through a Sulfatase‐Based Deracemization Process

et al. 2012

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“…Two (Solladié et al, 1990) and {[α] D +9 (c 1.0, CHCl 3 )} (Rudiyansyah and Garson, 2006). Known compound 5 was established as (3R), (5R)-5-hydroxy-de-O-methyllasiodiplodin from the spectroscopic evidence and by comparison with the reported literature (Yang et al, 2000).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxic lasiodiplodin derivatives from the fungus Syncephalastrum racemosum

Buayairaksa

Kanokmedhakul

et al. 2011

Arch. Pharm. Res.

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Chemical investigation of fungal biomass of the fungus Syncephalastrum racemosum led to the isolation of new natural products (3R),(5S)-5-hydroxy-de-O-methyllasiodiplodin (1), 6-oxode-O-methyllasiodiplodin (2), in addition to five known compounds, de-O-methyllasiodiplodin (3), lasiodiplodin (4), (3R),(5R)-5-hydroxy-de-O-methyllasiodiplodin (5), ergosterol (6), and ergosterol peroxide (7). Their structures were elucidated by spectroscopic techniques. The absolute configuration of 1 was determined by a modified Mosher's method. Compound 1 showed cytotoxicity against cholangiocarcinoma, KKU-M139, KKU-M156, and KKU-M213 cell lines with IC(50) values in the range of 14-19 μg/mL, while 3 showed cytotoxicity against KB, BC1, and NCI-H187 cell lines with IC(50) values of 12.67, 9.65, and 11.07 μg/mL, respectively.

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“…The first asymmetric total synthesis of de-O-methyllasiodiplodin (44), a precursor in the synthesis of lasiodiplodin (43), was published in 1990; this synthesis involved 18 steps with 0.8% overall yield [98] ; however, the synthetic route was too complicated, and the yield was too low. A shorter route using the RCM reaction as the key step was reported by Alois Fürst-ner and Kindler later, in 1996 [99] .…”

Section: Chemical Synthesismentioning

confidence: 99%

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

Jiang

Zhang

et al. 2014

Acta Pharmacol Sin

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Macrolides, which comprise a family of lactones with different ring sizes, belong to the polyketide class of natural products. Resorcinolic macrolides, an important subgroup, possess interesting structures and exhibit a wide variety of bioactivities, such as anti-tumor, anti-bacteria, and anti-malaria activities, etc. This review summarizes progress in isolation, bioactivity studies, biosynthesis, and representative chemical syntheses of this group of macrolides in recent decades, encompassing 63 naturally occurring macrolides published in 120 articles.

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Asymmetric synthesis of orsellinic acid type macrolides: The example of lasiodiplodin

Cited by 66 publications

References 11 publications

Chemoenzymatic Asymmetric Total Synthesis of (R)‐Lasiodiplodin Methyl Ether through a Sulfatase‐Based Deracemization Process

Chemoenzymatic Asymmetric Total Synthesis of (R)‐Lasiodiplodin Methyl Ether through a Sulfatase‐Based Deracemization Process

Cytotoxic lasiodiplodin derivatives from the fungus Syncephalastrum racemosum

Recent progress regarding the bioactivities, biosynthesis and synthesis of naturally occurring resorcinolic macrolides

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