5.26 Cross Metathesis

Żukowska, Karolina; Grela, Karol

doi:10.1016/b978-0-08-097742-3.00527-9

Cited by 14 publications

(7 citation statements)

References 119 publications

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“…Isoflavone 16a , flavone 17 , and deprotected starting material 15b were separated by column chromatography. For the introduction of the prenyl group, an olefin cross metathesis reaction was used . Occasionally, coordinating groups in the substrate can lead to catalyst inhibition through coordination to the metathesis catalyst .…”

Section: Resultsmentioning

confidence: 99%

Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F

et al. 2020

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The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4′-methoxy-3′-prenylisoflavone) and erysubin F (7,4′-dihydroxy-8,3′-diprenylisoflavone) were synthesized for the first time, starting from mono- or di-O-allylated chalcones, and the structure of 5-deoxy-3′-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis. Their reaction with hypervalent iodine reagents affords isoflavones via a 2,3-oxidative rearrangement and the corresponding flavone isomers via 2,3-dehydrogenation. This enabled a synthesis of 7,4′-dihydroxy-8,3′-diprenylflavone, a non-natural regioisomer of erysubin F. Erysubin F (8), 7,4′-dihydroxy-8,3′-diprenylflavone (27), and 5-deoxy-3′-prenylbiochanin A (7) were tested against three bacterial strains and one fungal pathogen. All three compounds are inactive against Salmonella enterica subsp. enterica (NCTC 13349), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 90028), with MIC values greater than 80.0 μM. The diprenylated natural product erysubin F (8) and its flavone isomer 7,4′-dihydroxy-8,3′-diprenylflavone (27) show in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) at MIC values of 15.4 and 20.5 μM, respectively. In contrast, the monoprenylated 5-deoxy-3′-prenylbiochanin A (7) is inactive against this MRSA strain.

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Section: Resultsmentioning

confidence: 99%

Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F

et al. 2020

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“…8 The diastereoselective cyclopropanation of the allylic alcohol 4 could be achieved via the Simmons-Smith protocol, 9,10 and the diene required for RCM could be derived from the epoxide 5. It is interesting to note that epoxide 5 could be assembled by cross metathesis (CM) using olefins 6 and 7, 11 both of which could be derived from the optically active oxiranes (8 and ent-8) We were pleased to find that Swern oxidation of 3 proceeded smoothly to give the cyclopropyl ketone 15 (Scheme 4). 22 This is important because previously unsuccessful attempt to oxidize a similar alcohol to the ketone has been reported (eq 1), 7b and the main difference between the two substrates is the stereochemistry of the neighbouring carbons.…”

Section: Resultsmentioning

confidence: 99%

Enantioselective synthesis of (+)-brevipolide H

Chen

Hou

2016

Org. Biomol. Chem.

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The enantioselective synthesis of natural brevipolide H is reported for the first time. By way of Sharpless epoxidation of penta-1,4-dien-3-ol, both enantiomerically pure epoxides were converted to the corresponding olefins for cross metathesis. Subsequent transformations, including epoxide ring opening, esterifications, cyclopropanation, oxidation and ring-closing metathesis, provided the target molecule. This synthesis successfully addresses previous shortcomings in preparing brevipolides.

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“…Having access to the building block 11 , we focused on its conversion to the targeted Asu derivatives through cross metathesis (CM) [ 20 ] with conjugated olefins 13a–d ( Scheme 2 ). In recent years, the cross-metathesis reaction has emerged as a valuable tool in the preparation of α-amino acids [ 21 – 27 ] and few useful general guidelines have emerged from these studies.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

Chattopadhyay

Sil

Mukherjee

2017

Beilstein J. Org. Chem.

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A new synthesis of the important amino acid 2-aminosuberic acid from aspartic acid is reported. The methodology involves the alternate preparation of (S)-2-aminohept-6-enoate ester as a building block and its diversification through a cross-metathesis reaction to prepare the title compounds. The utility of the protocol is demonstrated through the preparation of three suberic acid derivatives of relevance to the design and the synthesis of peptides of biological relevance.

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5.26 Cross Metathesis

Cited by 14 publications

References 119 publications

Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F

Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F

Enantioselective synthesis of (+)-brevipolide H

Synthesis of 2-aminosuberic acid derivatives as components of some histone deacetylase inhibiting cyclic tetrapeptides

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