The first synthesis of ent-agelasine F

Proszenyák, Ágnes; Brændvang, Morten; Charnock, Colin; Gundersen, Lise‐Lotte

doi:10.1016/j.tet.2008.10.081

Cited by 27 publications

(22 citation statements)

References 17 publications

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“…548 Tedania ignis (Sweeting Cay, Grand Bahama Is.) 555 The norsesterterpenoids irciformonin E-K 621-627 were isolated from Ircinia formosana (Taiwan), of which irciformonin I was found to inhibit peripheral blood mononuclear cell proliferation. 549 Dysidea cf.…”

Section: Red Algaementioning

confidence: 99%

Marine natural products

et al. 2011

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Section: Red Algaementioning

confidence: 99%

Marine natural products

et al. 2011

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“…It was clear to us that the synthetic strategy for racemic agelasine F could not readily be modified for synthesis of the (–)‐ or (+)‐isomers. Previously we searched for readily available enantiopure monoterpenes as a starting point and we have synthesized ent ‐agelasine F [(+)‐agelasine F] from commercially available ( R )‐pulegone ( 7 ) . Some steps in the synthesis of the desired enantiomer of the key‐intermediate 5 are shown in Scheme .…”

Section: Introductionmentioning

confidence: 99%

“…Some steps in the synthesis of the desired enantiomer of the key‐intermediate 5 are shown in Scheme . As a continuance of our work directed to synthesis of agelasines and analogs, and evaluation of their biological activities, we herein present the first total synthesis of the naturally occurring (–)‐agelasine F.…”

Section: Introductionmentioning

confidence: 99%

The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

Paulsen

Gundersen

2020

Eur J Org Chem

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Agelasine F (also known as ageline A) is a diterpene-adenine hybrid natural product isolated from marine sponges (Agelas species) and this compound is known to display cytotoxic activity against a variety of cancer cell lines as well as microorganisms. We herein report the first total synthesis of (-)-agelasine F. The commercially available and inexpensive monoterpenoid (S)-carvone was found to be a highly suitable starting material for the construction of the terpenoid part [a]

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“…However, introducing an alkoxy group on N 6 of a 9-substituted purine results mainly in the desired 7-alkylation, and the alkoxy group can be removed after the alkylation. To date, all agelasines and analogs have been prepared by this method [13,14].…”

Section: Introductionmentioning

confidence: 99%

2-Substituted agelasine analogs: Synthesis and biological activity, and structure and reactivity of synthetic intermediates

Roggen

Bohlin

Burman

et al. 2011

Pure and Applied Chemistry

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2-Substituted N-methoxy-9-methyl-9H-purin-6-amines were synthesized either from their corresponding 6-chloro-9-methyl-9H-purines or 2-chloro-N-methoxy-9-methyl-9H-purin-6-amine. Great diversity in the amino/imino tautomeric ratios was observed and calculated based on 1 H NMR. The tautomers were identified by 1D and 2D 1 H, 13 C, and 15 N NMR techniques, and showed significant variation both in 13 C and 15 N shift values. Comparison of the tautomeric ratios with Hammett F values revealed that as the field/inductive withdrawing abilities of the 2-substituent increased, the ratio of amino:imino tautomers was shifted toward the amino tautomer. Computational chemistry exposed the significance of hydrogen bonding between solvent and the compound in question to reach accurate predictions for tautomeric ratios. B3LYP/def2-TZVP density functional theory (DFT) calculations resulted in quantitatively more accurate predictions than when employing the less expensive BP86 functional. N-7-Alkylation of the 2-substituted N-methoxy-9-methyl-9H-purin-6amines showed that when the field/inductive withdrawing ability of the 2-substituent reached a certain point the reactivity drastically dropped. This correlated with the atomic charges on N-7 calculated using a natural bond orbital (NBO) analysis. Biological screening of the final 2-substituted agelasine analogs indicated that the introduction of a methyl group in the 2-position is advantageous for antimycobacterial and antiprotozoal activity, and that an amino function may improve activity against several cancer cell lines.

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The first synthesis of ent-agelasine F

Cited by 27 publications

References 17 publications

Marine natural products

Marine natural products

The First Synthesis of (–)‐Agelasine F; an Antimycobacterial Natural Product Found in Marine Sponges in the Agelas Genus

2-Substituted agelasine analogs: Synthesis and biological activity, and structure and reactivity of synthetic intermediates

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