Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant

Aitken, R. A.; Bouquet, Jaufret; Frank, Julia; Gidlow, Anna L. G.; Powder, Yomica L.; Ramsewak, Russel S.; Reynolds, William F.

doi:10.1039/c3ra41325j

Cited by 4 publications

(3 citation statements)

References 19 publications

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“…The compound was prepared as previously described [1] and was obtained directly by evaporation of a solution in ethanol as colourless prisms suitable for X-ray diffraction. The unit cell contained two closely similar independent molecules (the RMS between the two independent molecules, excluding H atoms is 0.11(1)), each involved in both intramolecular and intermolecular hydrogen bonding (Figure 2).…”

Section: Resultsmentioning

confidence: 99%

“…Some time ago we described the isolation, structure determination and synthesis of an unusual trichlorodihydroxybibenzyl derived from a terrestrial plant native to Trinidad [1]. In the course of the synthesis, the corresponding symmetrical dichlorodihydroxybibenzyl 1 (Figure 1) was obtained as a byproduct and subjected to full spectroscopic characterisation.…”

Section: Introductionmentioning

confidence: 99%

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2,2′-(Ethane-1,2-diyl)bis(4-chlorophenol)

Aitken

Gidlow

Ramsewak

et al. 2022

Molbank

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

2,2′-(Ethane-1,2-diyl)bis(4-chlorophenol)

Aitken

Gidlow

Ramsewak

et al. 2022

Molbank

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“…In another collaborative study with Dr Russel Ramsewak, following his visit to the University of the West Indies, the structure of the unusual trichlorodihydroxybibenzyl 58 isolated from a terrestrial plant was confirmed by total synthesis. 51 Alan's first research council-funded project examined an early example of what would now be termed organocatalysis, where highly functionalised achiral meso compounds were subjected to methanolysis in the presence of cinchona alkaloids. As shown in the example of 59 the resulting product containing six contiguous stereocentres is formed in reasonable enantiomeric excess, which for crystalline examples could be enhanced to a useful level by simple recrystallisation.…”

Section: O Phmentioning

confidence: 99%

A tribute to Professor Aitken

Karodia

2023

Arkivoc

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Robert Alan Aitken was born on 27th March 1958 to a farming family in the Dumfries and Galloway area of Southwest Scotland. Despite his rural upbringing, he was not the first scientist in the family since his great grandfather's younger brother, Edward Hamilton Aitken ("EHA", 1851("EHA", -1909, was a noted author and naturalist in India in the days of the Raj and a founder member and first Secretary (1883-1886) of the Bombay Natural History Society. He gave his name to several biological species including five species of Indian ant and a mosquito Anopheles aitkenii. When it came time for university, Alan followed the example of the only previous family member to go to a UK university, his paternal grandmother Rona Macrae (MA, 1925), and went to the University of Edinburgh. There he completed a BSc (1979) with a final year research project on stabilised phosphonium ylides and this was followed by a PhD (1982) on flash vacuum pyrolysis of cyclic sulfones, both projects jointly supervised by Dr Ian Gosney and Professor J. I. G. (later Sir John) Cadogan. He then obtained a Fulbright Scholarship for postdoctoral studies with Professor Albert I. Meyers at Colorado State University, Fort Collins (1982-84) in the area of asymmetric synthesis using nitrogen heterocycles. In 1984 he was awarded a Royal Society Warren Research Fellowship and joined the staff at the University of St Andrews, the first new staff appointment there since 1972. He has remained there ever since and is currently Reader in Organic Chemistry. He has been a Fellow of the Royal Society of Chemistry since 1997.Alan has maintained a small but productive research group and has so far supervised the research of 10 postdoctoral researchers, 29 PhD students, 9 MSc and MPhil students and 145 undergraduate project students. These include coworkers from over 20 countries: Belgium,

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Macrocyclic Olefin Metathesis at High Concentrations by Using a Phase‐Separation Strategy

Raymond¹,

Holtz-Mulholland²,

Collins³

2014

Chemistry A European J

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Macrocyclic olefin metathesis has seen advances in the areas of stereochemistry, chemoselectivity, and catalyst stability, but strategies aimed at controlling dilution effects in macrocyclizations are rare. Herein, a protocol to promote macrocyclic olefin metathesis, one of the most common synthetic tools used to prepare macrocycles, at relatively high concentrations (up to 60 mM) is described by exploitation of a phase-separation strategy. A variety of macrocyclic skeletons could be prepared having either different alkyl, aryl, or amino acids spacers.

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Isolation, structure determination and synthesis of a trichlorodihydroxybibenzyl from a terrestrial plant

Abstract: A new natural product isolated from the leaves of the plant Anthurium aripoense found in Trinidad is shown by spectroscopic analysis and total synthesis to be 29,5,69-trichloro-2,39-dihydroxybibenzyl, a structure unprecedented in a higher plant.

Cited by 4 publications

References 19 publications

2,2′-(Ethane-1,2-diyl)bis(4-chlorophenol)

2,2′-(Ethane-1,2-diyl)bis(4-chlorophenol)

A tribute to Professor Aitken

Macrocyclic Olefin Metathesis at High Concentrations by Using a Phase‐Separation Strategy

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