Total Synthesis of (±)-Batrachotoxinin A

Kurosu, Masaaki; Marcin, Lawrence R.; Grinsteiner, Timothy J.; Kishi, Yoshito

doi:10.1021/ja981258g

Cited by 82 publications

(52 citation statements)

References 26 publications

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“…IMDA cycloadducts derived from heteroatoms in tether of furans have recently been of great interest [3,4] since they involve in ring formation for natural product synthesis such as Azadirachtin [5], Fraquinocin E [6], Isoquinolin Alkoloids [7], (^)-Bathrachotoxinin A [8], Chatancin [9], etc. Additionally, the cycloadducts from IMDA reaction of furans are versatile intermediate in the preperation of carbohydrates and other biologically active compounds [10].…”

Section: Introductionmentioning

confidence: 99%

Structure and vibrational frequencies of 6-chloro-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene: density functional theory study

Arslan

Demircan

2008

Molecular Simulation

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The Fourier transform infrared (FT-IR) spectrum of 6-chloro-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene has been recorded in the region 4000-525 cm 21 . The optimised geometry, frequency and intensity of the vibrational bands of the title compound have been calculated using the ab initio Hartree -Fock and the density functional theory method with 6-31G(d,p) and 6-311G(d,p) basis set levels. The harmonic vibrational frequencies were calculated and the scaled values have been compared with experimental FT-IR spectrum. The observed and the calculated frequencies are found to be in good agreement. The theoretical vibrational spectrum of the title compound were interpreted by means of potential energy distributions using VEDA 4 program.

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Section: Introductionmentioning

confidence: 99%

Structure and vibrational frequencies of 6-chloro-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene: density functional theory study

Arslan

Demircan

2008

Molecular Simulation

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“…Accordingly, de novo chemical synthesis of the toxin and related structures is the only current available strategy for accessing such probes. [16] …”

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confidence: 99%

Inhibition of Sodium Ion Channel Function with Truncated Forms of Batrachotoxin

Toma

Logan

Ménard

et al. 2016

ACS Chem. Neurosci.

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A novel family of small molecule inhibitors of voltage-gated sodium channels (Navs) based on the structure of batrachotoxin (BTX) – a well-known channel agonist – is described. Protein mutagenesis and electrophysiology experiments reveal the binding site as the inner pore region of the channel, analogous to BTX, alkaloid toxins, and local anesthetics. Homology modeling of the eukaryotic channel based on recent crystallographic analyses of bacterial NaVs suggests a mechanism of action for ion conduction block.

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“…The 1,4-oxazepane ring is a seven-membered heterocycle containing nitrogen and oxygen in 1,4-positions, which is endowed with a wide range of biological activities, [63][64][65] and it is found in diverse natural products such as the neurotoxin (±)-batrachotoxinin A 32, 66 as well as, synthetic derivatives like derivatives 33 and 34 acting as peripheral-selective noradrenaline reuptake inhibitors 67 and the sordarin analog 35 which showed a potent antifungal activity against Candida albicans, 68 ( Figure 7). Although many synthetic methods for this N,O-heterocycle have been documented, most of them are focused on fused benzoxazepine derivatives.…”

Section: A Straightforward Synthesis Of 47-disubstituted 14-oxazepamentioning

confidence: 99%

Recent contributions to the Diversity-Oriented Synthesis (DOS) mediated by iminium ions through multicomponent Mannich-type reactions

Abonı́a¹,

Castillo²,

Kotali³

2017

Arkivoc

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This short account summarizes the most recent contributions of the author and his collaborators to the Diversity Oriented Synthesis (DOS) mediated, at least in a step of the process, by Mannich-type reactions (MTR) and using formaldehyde as common starting material in all cases. Through this strategy, diverse nitrogen-containing acyclic and heterocyclic systems were synthesized, whether in straightforward or multicomponent approaches.

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Total Synthesis of (±)-Batrachotoxinin A

Cited by 82 publications

References 26 publications

Structure and vibrational frequencies of 6-chloro-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene: density functional theory study

Structure and vibrational frequencies of 6-chloro-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene: density functional theory study

Inhibition of Sodium Ion Channel Function with Truncated Forms of Batrachotoxin

Recent contributions to the Diversity-Oriented Synthesis (DOS) mediated by iminium ions through multicomponent Mannich-type reactions

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