Author
Bryan M. Gatehouse
Bio: Bryan M. Gatehouse is an academic researcher from Monash University, Clayton campus. The author has contributed to research in topics: Crystal structure & Denticity. The author has an hindex of 21, co-authored 92 publications receiving 1346 citations.
Papers published on a yearly basis
Papers
More filters
••
TL;DR: In this paper, the α-stereochemistry of progesterone derivatives has been established by a full X-ray structural analysis of the α-(4-6η)Pd(acac) derivative of Progestone (Hacac = pentane-2,4-dione).
Abstract: [6β-2H]- and [6α-2H]-Cholest-4-en-3-one react with palladium(II) chloride in dry tetrahydrofuran to give the α-(4–6η)-PdCl compound with highly stereoselective loss of the 6β-deuteron or proton; the α-stereochemistry-has been firmly established by a full X-ray structural analysis of the α-(4–6η)Pd(acac) derivative of progesterone (Hacac = pentane-2,4-dione).
5 citations
••
TL;DR: The structure of fruticosonine, a new type of indole alkaloid from A. fruticosa, has been determined by X-ray crystallography and by synthesis as discussed by the authors.
Abstract: The structure of fruticosonine, a new type of indole alkaloid from A. fruticosa, has been determined by X-ray crystallography and by synthesis.
5 citations
••
TL;DR: Bicyclo[2.2.1] was used to synthesize 5-(bicyclopentadiene) at 570o/0.01 mm for pyrolysis as mentioned in this paper, which gave acetone, carbon dioxide, furan and butatrienone.
Abstract: Bicyclo[2.2.l]hept-5-en-2-one was condensed with 2,2-dimethyl-1,3-dioxan-4,6-dione in the presence of titanium tetrachloride/pyridine to yield 5-(bicyclo[2.2.1]hept-5'-en-2'-ylidene)-2,2-dimethyl-1,3- dioxan-4,6-dione (6a) which on pyrolysis at 520-560o/0.01 mm gave acetone, carbon dioxide, cyclopentadiene and butatrienone. In the same way 5-(7'-oxabicyclo[2.2.1]hept-5'-en-2'-ylidene)-2,2- dimethyl-1,3-dioxan-4,6-dione (6b) was prepared from 7-oxabicyclo[2.2.1]hept-5-en-2-one and on pyrolysis at 570o/0.01 mm it gave acetone, carbon dioxide, furan and butatrienone. Alkylation of 2-trimethylsiloxybicyclo[2.2.1]hepta-2,5 with phenylthiomethyl chloride with titanium tetrachloride as catalyst followed by condensation with 2,2-dimethyl-1,3-dioxan-4,6-dione gave an endo/exo mixture of 5-(3'-phenylthiomethylbicyclo[2.2.1]hept-5'-en-2'-ylidene)-2,2-dimethy 1-1,3-dioxan- 4,6-dione. The structure of the endo isomer was established by X-ray crystallography. Oxidation of the phenylthiomethyl compound with m-chloroperbenzoic acid yielded the sulfoxide which was converted by boiling in carbon tetrachloride into 5-(3'-methylenebicyclo[2.2.l]hept-5'-en-2'-ylidene)- 2,2-dimethyl-1,3-dioxan-4,6-dione (8). Preliminary studies on the fragmentation of compound (8) have shown that at 450o/0.01 mm it is converted into acetone, carbon dioxide and products showing ketene absorption at 2140 cm-1. The formation of pentatetraenone has not been established with certainty. The 3'-phenylsulfonylmethyl, phenylselenyl and methyl derivatives of (6a) are also described.
4 citations
••
TL;DR: In this paper, a series of dicarbonyl(triphenylphosphine) and 1,3-di-t-butyl-2-methoxyarene chromium compounds were shown to exhibit dynamic behavior which is interpreted in terms of kinetic restrictiln of rotation about the arene-mETHoxy bond, and similar behaviour is observed in a chelated aryl chromium analogue of these compounds.
Abstract: Low-temperature1H n.m.r. spectra of a series of dicarbonyl(triphenylphosphine)(1,3-di-t-butyl-2-methoxyarene)chromium compounds exihibit dynamic behaviour which is interpreted in terms of kinetic restrictiln of rotation about the arene–methoxy bond, and similar behaviour is observed in a chelated aryl chromium analogue of these compounds; this explanation is supported by anX-ray crystal structure of dicarbonyl (triohenylphosphine)(1,3-di-t-butyl-2 methoxybenzene) chromium in which the O–CH3group is syn to the chromium.
3 citations
••
TL;DR: In this article, the structure of the first heteropolyanion with an X:M ratio of 1:2 was determined from single crystal X-ray studies of the sodium salt; the idealized anion has 2m symmetry and consists of a shell of WO6 octahedra and PO4 tetrahedra made up of four PW2O13 groups linked by corner sharing and a sodium atom is situated in the centre of the polyanion.
Abstract: The structure of the first heteropolyanion, [P4W8O40]12–, with an X:M ratio of 1:2, has been determined from single crystal X-ray studies of the sodium salt; the idealized anion has 2m symmetry and consists of a shell of WO6 octahedra and PO4 tetrahedra made up of four PW2O13 groups linked by corner sharing and a sodium atom is situated in the centre of the polyanion.
2 citations
Cited by
More filters
••
4,522 citations
••
TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Abstract: In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
2,268 citations
••
TL;DR: In this paper, the preparation of a colloidal colloidal by un procede sol gel is described, and a procedure for determination des proprietes electriques et electrochimiques is described.
2,040 citations
••
TL;DR: The power of cascade reactions in total synthesis is illustrated in the construction of complex molecules and underscore their future potential in chemical synthesis.
Abstract: The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.
1,762 citations
••
TL;DR: The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which has yet to be eclipsed by any other transformation in the current synthetic repertoire as mentioned in this paper.
Abstract: The Diels-Alder reaction has both enabled and shaped the art and science of total synthesis over the last few decades to an extent which, arguably, has yet to be eclipsed by any other transformation in the current synthetic repertoire. With myriad applications of this magnificent pericyclic reaction, often as a crucial element in elegant and programmed cascade sequences facilitating complex molecule construction, the Diels-Alder cycloaddition has afforded numerous and unparalleled solutions to a diverse range of synthetic puzzles provided by nature in the form of natural products. In celebration of the 100th anniversary of Alder's birth, selected examples of the awesome power of the reaction he helped to discover are discussed in this review in the context of total synthesis to illustrate its overall versatility and underscore its vast potential which has yet to be fully realized.
1,427 citations