Synthetic studies towards batrachotoxin 1. A furan-based intramolecular diels-alder route to construct the a-d ring system

Grinsteiner, Timothy J.; Kishi, Yoshito

doi:10.1016/s0040-4039(00)74400-5

Cited by 37 publications

(10 citation statements)

References 17 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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“…In fact proclivity of furans to undergo [2–4] cycloaddition with various π-bonds has attracted the attention of many research groups, as it allows for the rapid construction of valuable synthetic intermediates [2–4]. In view of furans electron-rich constitution and electron donor properties they have been involved mostly as the diene component in the cycloaddition process [5,6]. In this context, we have been studying on synthesis of heterotricyclicfused compounds [7,8].…”

Section: Introductionmentioning

confidence: 99%

The Molecular Structure and Vibrational Spectrum of 6-bromo-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene

Arslan

Demircan

2007

IJMS

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Geometric parameters and FT-IR spectrum of 6-bromo-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene were computed by the HF, B3LYP, B3PW91 and mPW1PW91 methods in conjunction with the 6-31G(d,p) basis set. The calculated IR spectra are in a good agreement with the observed FT-IR spectrum. A general better performance of B3LYP, B3PW91 and mPW1PW91 versus HF was quantitatively characterized by using PAVF 1.0 program. Optimal uniform scaling factors calculated for the title compound are 0.8952, 0.9552, 0.9520 and 0.9456 for HF, B3LYP, B3PW91 and MPW1PW91 methods, respectively.

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“…Kishis 1998 total synthesis of racemic batrachotoxinin A: The synthesis of batrachotoxinin A (241) from the WielandMiescher ketone (30) [23,77] relied on 1) a stereoselective intramolecular furan Diels-Alder reaction to construct the steroidal architecture and 2) an intramolecular oxy-Michael reaction to close the oxazapane heterocycle. To address the first objective, a complex 3,4-disubstituted furan (277) was prepared according to the protocol specified by Garst and Spencer in 1973 [78] (Scheme 26).…”

Section: Synthetic Studies Targeting the Batrachotoxin Family Of Cardmentioning

confidence: 99%

Chemical Synthesis of the Cardiotonic Steroid Glycosides and Related Natural Products

Heasley

2012

Chemistry A European J

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The active components from the extracts of Digitalis, cardiotonic steroid glycosides, have been ingested by humans for more than 200 years as a medicinal therapy for heart failure and abnormal heart rhythms. The positive inotropic activity of the cardiotonic steroids that mediates clinically useful physiological effects in patients has been attributed largely to a high affinity inhibitory interaction with the extracellular surface of the membrane-bound sodium pump (Na(+)/K(+)-ATPase). However, previously unrecognized intracellular signaling pathways continue to be uncovered. This Review examines both partial and de novo synthetic approaches to the medicinally important and structurally captivating cardenolide and bufadienolide steroid families, with an emphasis on the stereocontrolled construction of the pharmacophoric aglycone (genin) framework.

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Synthetic studies towards batrachotoxin 1. A furan-based intramolecular diels-alder route to construct the a-d ring system

Cited by 37 publications

References 17 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

The Molecular Structure and Vibrational Spectrum of 6-bromo-8-thia-1,4-epoxybicyclo[4.3.0]non-2-ene

Chemical Synthesis of the Cardiotonic Steroid Glycosides and Related Natural Products

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