Synthesis and Structure Revision of the C43–C67 Part of Amphidinol 3

Ebine, Makoto; Kanemoto, Masashi; Manabe, Yoshiyuki; Konno, Yoshihiro; Sakai, Ken; Matsumori, Nobuaki; Murata, Michio; Oishi, Tohru

doi:10.1021/ol401176a

Cited by 29 publications

(20 citation statements)

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“… Confirmation of the structural revision of 4 using DP4 calculations. Shown are the diastereomers A–D for the relative configuration revision at C51 and the DP4 probability supporting the structural revisions made by Ebine et al 5a. Also shown are the original J BCA for 4 : 2 J (C51,H50) value of −2.5 Hz is considered an intermediate value, thus resulting in the misassignment of C51.…”

supporting

confidence: 55%

Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical‐Shift Analysis: Insights into their Mechanism of Action

Waters

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et al. 2015

Angewandte Chemie

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In bloom:Harmful algal bloom toxins derived from the dinoflagellate Karlodinium sp. produce an interesting suite of complex polyketides whichhave been shown to have hemolytic,cytotoxic and ichthyotoxic activity.Better understanding the mechanism of action for this class of compounds could lead to the development of new agents for targeting cancer-cell membranes. Ready,Set, Go! Herein, we found in aset of p-conjugated phenylaza[18]crown-6-1,2,3-triazol-fluoroionophores, which possess in ortho positionoft he aniline moiety an alkoxyg roup, an enhanced K + /Na + selectivitiy with increasing steric hindrance of the alkoxy group (MeO < EtO < iPrO) and ad ecrease of the K + -complex stability.Chem. Asian J.

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supporting

confidence: 55%

Stereochemical Studies of the Karlotoxin Class Using NMR Spectroscopy and DP4 Chemical‐Shift Analysis: Insights into their Mechanism of Action

Waters

Place

et al. 2015

Angewandte Chemie

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“…Because the absolute configuration of the B ring of KmTx2 is antipodal to that of AM3, we have confirmed the absolute configuration of the B ring of AM3 to be correct by degradation of the natural product and chemical correlation . In contrast, the absolute configurations at C2 and C51 were revised to be R and S , respectively, by chemical syntheses of partial structures and chemical correlation (Figure b) ,. The reason for the misassignment at C51 was the difficulty in applying the JBCA method because the key J value was in the medium range (i.e., 3 J H50,H51 =3.4 Hz).…”

Section: Figurementioning

confidence: 99%

Synthesis and Stereochemical Revision of the C31–C67 Fragment of Amphidinol 3

et al. 2018

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Amphidinol 3( AM3) is am arine natural product produced by the dinoflagellate Amphidinium klebsii. Although the absolute configuration of AM3 was determined in 1999 by extensive NMR analysis and degradation of the natural product, it was adaunting task because of the presence of numerous stereogenic centers on the acyclic carbon chain and the limited availability from natural sources.T hereafter, revisions of the absolute configurations at C2 and C51 were reported in 2008 and 2013, respectively.Reported herein is the revised absolute configuration of AM3:3 2S,3 3R, 34S,3 5S, 36S,a nd 38S based on the chemical synthesis of partial structures corresponding to the C31-C67 fragment of AM3 in combination with degradation of the natural product. The revised structure is unique in that both antipodal tetrahydropyran counterparts exist on as ingle carbon chain. The structural revision of AM3 may affect proposed structures of congeners related to the amphidinols.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…Although total syntheses of marine natural products require extremely high-level work in organic chemistry, it will surely continue to be central to the confirmation of natural product structure assignment [e.g., 101,102], as well as providing material for biological testing toward pharmaceutical development, and investigations of biosynthetic pathways.…”

Section: Revised Structuresmentioning

confidence: 99%