Total Synthesis of (−)-Tetrodotoxin from <scp>d</scp>-Glucose: A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (−)-Tetrodotoxin

Akai, Shoji; Seki, Hidehito; Sugita, Naoki; Kogure, Tomokazu; Nishizawa, Naoki; Suzuki, Katsuhiko; Nakamura, Yutaka; Kajihara, Yasuhiro; Yoshimura, Juji; Sato, Kenichi

doi:10.1246/bcsj.20090194

Cited by 41 publications

(17 citation statements)

References 34 publications

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“…The spectral data of intermediate 238 were identical to those reported by Sato . However, it was noted that the NMR spectra of Sato's lactone as well as those of intermediate 238 were inconsistent with the structure.…”

Section: Synthesis Of Ttxsupporting

confidence: 72%

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Tetrodotoxin: History, Biology, and Synthesis

et al. 2019

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This review provides a comprehensive coverage of the history, biology and chemistry of tetrodotoxin (TTX). It traces the origin of this remarkable molecule all the way back to the ancient Chinese medicine records. The discovery of biological activity, isolation, and a brief overview of structure elucidation are summarized. Next, the biology of TTX is discussed, primarily in the context of its activity in the sodium channels, its anesthetic properties, and its potential use in cancer treatment or drug addiction. Biosynthesis of TTX is covered before the discussion of the total syntheses. All total, formal or partial syntheses are covered but those total syntheses that have been discussed in previous reviews are only briefly summarized. Finally, the synthesis of natural and unnatural derivatives is surveyed, and a conclusion and outlook are provided for this very extensive field of endeavor. To the best of our knowledge the literature coverage is complete up to December 2018.

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Section: Synthesis Of Ttxsupporting

confidence: 72%

“…In 2010 Sato published his latest synthesis, again using d ‐glucose ( 165 ) as a starting material (Scheme ) . d ‐Glucose ( 165 ) was transferred to ketone 177 by a known procedure .…”

Section: Synthesis Of Ttxmentioning

confidence: 99%

Tetrodotoxin: History, Biology, and Synthesis

et al. 2019

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“…Sato publizierte 2010 seine neueste Synthese, wieder ausgehend von d ‐Glucose ( 165 ) . d ‐Glucose ( 165 ) wurde über ein bekanntes Verfahren in das Keton 177 umgewandelt .…”

Section: Synthese Von Ttxunclassified

“…Die spektroskopischen Daten des Intermediats 238 waren identisch mit den von Sato beschriebenen . Allerdings wurde angemerkt, dass die NMR‐Spektren von Satos Lacton ebenso wie die des Intermediats 238 nicht mit der Struktur übereinstimmten.…”

Section: Synthese Von Ttxunclassified

Tetrodotoxin: Geschichte, Biologie und Synthese

et al. 2019

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Dieser Aufsatz bietet eine umfassende Übersicht über die Geschichte, Biologie und Chemie von Tetrodotoxin (TTX). Er verfolgt den Ursprung dieses bemerkenswerten Moleküls zurück bis zu altertümlichen Aufzeichnungen der chinesischen Medizin. Nach einem kurzen Überblick über die Entdeckung der biologischen Aktivität, die Isolierung und Strukturaufklärung wird die Biologie von TTX diskutiert, hauptsächlich im Zusammenhang mit seiner Wirksamkeit in Natriumkanälen, seiner anästhetischen Wirkung und dem Anwendungspotential in der Krebsbehandlung oder bei Medikamentenabhängigkeit. Der Diskussion der Biosynthese von TTX folgen Ausführungen zur Totalsynthese. Sämtliche Total‐, Formal‐ und Partialsynthesen werden aufgeführt, wobei wir aber diejenigen Totalsynthesen, die bereits in früheren Aufsätzen vorgestellt wurden, nur kurz zusammenfassen. Schließlich werden die Synthesen von natürlichen und nichtnatürlichen Derivaten betrachtet, und es wird eine Zusammenfassung mit Ausblick für dieses sehr umfangreiche Fachgebiet geboten. Nach bestem Wissen haben wir die Literatur bis Dezember 2018 vollständig abgedeckt.

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“…We have been synthesizing tetrodotoxin and its analogues for a long time. [10][11][12][13][14][15][16][17][18] In recent years, we have focused on developing a subtype selective blocker of a voltage-gated sodium channel based on tetrodotoxin and saxitoxin to analyze the biological functions. Concerning this issue, we have been interested in chiriquitoxin, because it is the sole example that possesses potassium-channel blocking activity among the tetrodotoxin family.…”

mentioning

confidence: 99%

Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog

Adachi

Imazu

Sakakibara

et al. 2014

Chemistry A European J

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The first total synthesis of chiriquitoxin, the most structurally complex analogue of tetrodotoxin isolated from a Costa Rican dart frog, has been accomplished from a newly designed intermediate for a variety of tetrodotoxin derivatives. The synthesis includes the third total synthesis of tetrodotoxin in this laboratory, and its intermediate was transformed into chiriquitoxin by a stereocontrolled aldol reaction with a D-camphor-derived lactone for installation of the unique side chain, and a new deprotection of methylthiomethyl (MTM) ether by using a Pummerer rearrangement.

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Total Synthesis of (−)-Tetrodotoxin from d-Glucose: A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (−)-Tetrodotoxin

Cited by 41 publications

References 34 publications

Tetrodotoxin: History, Biology, and Synthesis

Tetrodotoxin: History, Biology, and Synthesis

Tetrodotoxin: Geschichte, Biologie und Synthese

Total Synthesis of Chiriquitoxin, an Analogue of Tetrodotoxin Isolated from the Skin of a Dart Frog

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