Stereoselective Synthesis of 2-epi-Pena-residin A and Its (15R,16R)-Stereoisomer

林国强,; 刘定国,

doi:10.3987/com-97-s(n)24

Cited by 20 publications

(8 citation statements)

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“…Surprisingly, yields for this reaction were consistently lower when epoxide 10 was protected as the silyl ether despite some literature evidence to the contrary. [23][24][25] Diol 15 was protected in near quantitative yield as the acid-stable diacetate 16. Addition of an excess of Jones' reagent to a concentrated solution of 16 in acetone led to both the cleavage of the acetal group and oxidation of the resultant aldehyde to the carboxylic acid 17, which was subsequently converted in 97% yield to methyl ester 18 after reaction with diazomethane.…”

Section: Synthesis Of Lipoxin a 4 Analoguementioning

confidence: 99%

Aromatic Lipoxin A₄and Lipoxin B₄Analogues Display Potent Biological Activities

et al. 2007

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Lipoxins are a group of biologically active eicosanoids typically formed by transcellular lipoxygenase activity. Lipoxin A4 (LXA4) and Lipoxin B4 (LXB4) biosynthesis has been detected in a variety of inflammatory conditions. The native lipoxins LXA4 and LXB4 demonstrate potent antiinflammatory and proresolution bioactions. However, their therapeutic potential is compromised by rapid metabolic inactivation by PG dehydrogenase-mediated oxidation and reduction. Here we report on the stereoselective synthesis of aromatic LXA4 and LXB4 analogues by employing Sharpless epoxidation, Pd-mediated Heck coupling, and diastereoselective reduction as the key transformations. Subsequent biological testing has shown that these analogues display potent biological activities. Phagocytic clearance of apoptotic leukocytes plays a critical role in the resolution of inflammation. Both LXA4 analogues (1R)-3a and (1S)-3a were found to stimulate a significant increase in phagocytosis of apoptotic polymorphonuclear leukocytes (PMN) by macrophages, with comparable efficacy to the effect of native LXA4, albeit greater potency, while the LXB4 analogue also stimulated phagocytosis with a maximum effect observed at 10-11 M. LX-stimulated phagocytosis was associated with rearrangement of the actin cytoskeleton consistent with that reported for native lipoxins. Using zymosan-induced peritonitis as a murine model of acute inflammation (1R)-3a significantly reduced PMN accumulation.

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Section: Synthesis Of Lipoxin a 4 Analoguementioning

confidence: 99%

Aromatic Lipoxin A₄and Lipoxin B₄Analogues Display Potent Biological Activities

et al. 2007

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“…20 In 1998, Lin and co-workers synthesized epimers 7 and 8 due to issues with cyclizing the azetidine core of all other isomers. 8 Similarly to penaresidin A (1), penaresidin B (2) was shown to be an ATPase-activator and a potential biomarker for serum metabolism in patients with cervical cancer. 1,7 Additionally, penaresidin B (2) displayed cytotoxicity against murine lymphoma L1210 cells.…”

Section: Biological Activity Of Penaresidin a Penaresidin B And Penaz...mentioning

confidence: 99%

Synthesis and Biological Activity of Penaresidins A and B, Penazetidine A, and Related Analogues

Burns,

McClure,

Parikh

et al. 2024

Synthesis

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Since the first reports of their isolation, penaresidins A and B together with penazetidine A and related analogues have attracted interest from the synthetic community for their unique structural features, specifically the highly functionalized azetidine core. This review provides a comprehensive overview of the biological activity of the penaresidins, penazetidine, and their analogues together with reported synthetic strategies developed since their isolation.1 Introduction2 Biological Activity of Penaresidin A, Penaresidin B, and Penazetidine A and Related Analogues3 Retrosynthetic Analysis4 Penaresidin A Analogue (Kamikawa, 1995)5 15-epi-Penaresidin A (Mori, 1995)6 16-epi-Penazetidine A (Mori, 1996)7 Penaresidin B (Yoda, 1997)8 15-epi-Penaresidin B and Penaresidin B (Mori, 1997)9 Penaresidin A and 16-nor-Penazetidine A (Knapp, 1997)10 Substituted Penaresidin Core (Beauhaire and Ducrot, 1998)11 Substituted Penaresidin Core (Ducrot, 1999)12 Penaresidin A (Lin, 1999)13 Penaresidin B (Yoda, 2003)14 Penaresidin Structure-Reactivity Relationship (Kobayashi, 2007)15 Penaresidin A (Raghavan, 2010)16 Penaresidin A (Reddy, 2014)17 Penaresidin B (Liu, 2015)18 Penaresidin B (Yakura, 2018)19 Penaresidin B (DuBois, 2020)20 Penaresidin Analogues (Bodnár, 2021)

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“…Lin et al reported that the SN2type cyclization is strongly influenced by the substitution pattern of the precursors in the synthesis of penaresidins 1, 6, and 7 (Scheme 12). 24,31 To synthesize 6 and 7, N-Ts-1-O-TBS-3-O-Bn-2,3-anti-3,4-syn-4-amino precursor 131 was prepared from 1,4-pentadien-3-ol (90). According to the literature, 32 90 was selectively converted into epoxide 125 by Sharpless asymmetric epoxidation.…”

Section: Construction Of Azetidine Rings From 4-amino Precursorsmentioning

confidence: 99%

“…Scheme 12. Synthesis of penaresidins 6 and 7 using SN2-type cyclization of 2,3-anti-3,4-syn-precursor 131 and the unsuccessful cyclization of 2,3-syn-3,4-syn-precursor 134 24,31 Yoda and colleagues succeeded in the cyclization of 2,3-syn-3,4-syn-4-amino precursor 140 having Boc and MOM groups as N-and O-protecting groups, respectively, in the synthesis of 2 from 2,3,5-tri-O-benzyl-D-arabinofuranose (136) (Scheme 13). 33 Scheme 14.…”

Section: Construction Of Azetidine Rings From 4-amino Precursorsmentioning

confidence: 99%

Synthesis of Sphingosine-Related Azetidine Alkaloids, Penaresidins: Construction of Highly Substituted Azetidine Rings

Yakura¹,

Fujiwara²

2020

HETEROCYCLES

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Penaresidin A and B are sphingosine-related natural products that contain a 2,3,4-trisubstituted azetidine ring and a long alkyl side chain.Stereoselective construction of the trisubstituted azetidine ring is a crucial step in the synthesis of penaresidins, and all the currently reported syntheses have been accomplished by SN2-type cyclization of a precursor having a 1-amino-2,3-diol structure with three continuous stereocenters. This cyclization is strongly influenced by the configurations of the vicinal amino alcohol moieties of the precursors. This review focuses on the SN2-type cyclizations that are used to construct the trisubstituted azetidine ring in penaresidin synthesis.Dedicated to Professor Kaoru Fuji on the occasion of his 80th birthday. CONTENTS 1. Introduction 2. Construction of azetidine rings from 2-amino precursors 2.1 Construction after introduction of the side chain 2.2 Construction before introduction of the side chain 3. Construction of azetidine rings from 4-amino precursors 4. Conclusions

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Stereoselective Synthesis of 2-epi-Pena-residin A and Its (15R,16R)-Stereoisomer

Cited by 20 publications

References 0 publications

Aromatic Lipoxin A₄and Lipoxin B₄Analogues Display Potent Biological Activities

Aromatic Lipoxin A₄and Lipoxin B₄Analogues Display Potent Biological Activities

Synthesis and Biological Activity of Penaresidins A and B, Penazetidine A, and Related Analogues

Synthesis of Sphingosine-Related Azetidine Alkaloids, Penaresidins: Construction of Highly Substituted Azetidine Rings

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Stereoselective Synthesis of 2-epi-Pena-residin A and Its (15R,16R)-Stereoisomer

Cited by 20 publications

References 0 publications

Aromatic Lipoxin A4and Lipoxin B4Analogues Display Potent Biological Activities

Aromatic Lipoxin A4and Lipoxin B4Analogues Display Potent Biological Activities

Synthesis and Biological Activity of Penaresidins A and B, Penazetidine A, and Related Analogues

Synthesis of Sphingosine-Related Azetidine Alkaloids, Penaresidins: Construction of Highly Substituted Azetidine Rings

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Product

Resources

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Aromatic Lipoxin A₄and Lipoxin B₄Analogues Display Potent Biological Activities

Aromatic Lipoxin A₄and Lipoxin B₄Analogues Display Potent Biological Activities