A. W. McCulloch

New England Center for Clinical Research

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A. G. McInnes

Western Sydney University

David G. Smith

Heriot-Watt University

John A. Walter

Institute for Marine Biosciences

Donald G. Smith

Reid Health

Arlan S. Freitas

Instituto Federal do Maranhão

R. A. Matheson

University of Otago

A. W. Hanson

Kaken Pharmaceutical (Japan)

Michael A. Quilliam

National Research Council Canada

Branko Stanovnik

ACTA (United States)

David G. E. Smith

Heriot-Watt University

Cooperative Institutions

National Research Council Canada

Dalhousie University

Institute for Marine Biosciences

National Academies of Sciences, Engineering, and Medicine

Fisheries and Oceans Canada

Nova Scotia Department of Agriculture

University of British Columbia

University of Wisconsin–Madison

Science and Engineering Research Council

Natural Sciences and Engineering Research Council

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Structural studies of 1,3-dioxa-2-silacycloalkanes

Canadian Journal of Chemistry (1986)

A. W. Hanson A. W. McCulloch A. G. McInnes

Crystal structure analyses of 1,3-dioxa-2,2-diphenyl-2-sila-5,6-benzocycloheptane (1), 2,9-disila-1,3,8,10-tetraoxa-2,2,9,9-tetraphenyl-5,6,12,13-dibenzocyclotetradecane (2), 2,10-disila-2,2,10,10-tetramethyl-1,3,9,11-tetraoxa-5,7,13,15-dibenzocyclohexadecane (3), 2,7-disila-2,2,7,7-tetramethyl-1,3,6,8-tetraoxa-4,5,9,10-dibenzocyclodecane (4), and 2,4-disila-2,2,4,4-tetraphenyl-1,3,5-trioxa-6,7-benzocycloheptane (11) are reported. Facile acid-catalyzed reaction of 2,7-disila-1,3,6,8-tetraoxa-2,2,7,7-tetraphenyl-4,5,9,10-dibenzocyclodecane (8) with water gives 1,3-di(2-hydroxyphenoxy)-1,3-disila-2-oxa-1,1,3,3-tetraphenylpropane (12). The latter in turn decomposes in a base-catalyzed reaction to give a mixture of 11 and catechol.

Catechol

Base (topology)

10.1139/v86-239

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Citations (25)

The biosynthesis of caerulomycins in Streptomyces caeruleus. Isolation of a new caerulomycin and incorporation of picolinic acid and glycerol into caerulomycin A

Canadian Journal of Chemistry (1988)

L. C. Vining A. G. McInnes A. W. McCulloch Donald G. Smith John A. Walter

Oxidation with permanganate of caerulomycin A labeled biosynthetically from [U- 14 C]lysine in cultures of Streptomyces caeruleus yielded picolinic acid with the same specific activity as the antibiotic. [ 3 H]Picolinic acid was incorporated into caerulomycin A with high efficiency and the label was also found exclusively in picolinic acid after oxidation, implicating free picolinic acid as an intermediate in the pathway from lysine. The substituted pyridyl ring of caerulomycin was labeled by [2- 13 C, 1,3- 14 C]glycerol. 13 C nuclear magnetic resonance analysis located the 13 C predominantly at C-6, suggesting that C-5, C-6, and C-7 were derived from glycerol as an intact three-carbon precursor. Since no incorporation of [1- 13 C]glyceric acid was detected and [3- 13 C, 3- 14 C]methylglyoxal labeled the antibiotic only marginally, these compounds are probably not biosynthetic intermediates en route from glycerol. A new caerulomycin possessing an aldehyde in place of the aldoxime substituent at C-6 was isolated from culture broths and is postulated to be a late intermediate in the formation of caerulomycin A.

Picolinic acid

Glyceric acid

Permanganate

10.1139/v88-031

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Citations (26)

Zinc from oyster tissue as causative factor in mouse deaths in official bioassay for paralytic shellfish poison.

PubMed (1989)

A. W. McCulloch Robert K. Boyd Arlan S. Freitas R. A. Foxall W. D. Jamieson

Toxicity (extreme weakness, body temperature drop, cyanosis, some slow deaths) in test mice, upon intraperitoneal injection of standard-method paralytic shellfish poison (PSP) extracts of some PSP-free oysters, is consistent with the relatively high levels of zinc in these extracts. As a rough guideline, the threshold for a toxic response corresponds to a drained tissue zinc level of over 900 micrograms/g. The identification of zinc as the substance responsible has been supported by inducing toxicity in control extracts by spiking with nontoxic levels of zinc, and by eliminating toxicity from toxic extracts by chemical removal (precipitation, ion exchange) of metals.

Zinc toxicity

Source

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Citations (27)

ChemInform Abstract: THE ACTION OF HYPOCHLORITE ON M‐CRESOL. PART 2. MUCONIC ACID DERIVATIVES

Chemischer Informationsdienst (1981)

George M. Strunz Masatoshi Kakushima Alan D. Gibson A. W. McCulloch Peter S. White

Muconic acid

10.1002/chin.198119131

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Influence of Lewis acids on the Diels–Alder reaction. II. Rearrangement of 1- and 1,4-substituted diethyl 7-oxabicyclo[2•2•1]2,5-heptadiene-2,3-dicarboxylate adducts to 4- and 4,6-substituted diethyl 3-hydroxyphthalates

Canadian Journal of Chemistry (1969)

A. W. McCulloch Branko Stanovnik David G. Smith A. G. McInnes

Direct formation of 4- or 4,6-alkyl and aryl substituted diethyl 3-hydroxyphthalates from the correspondingly substituted Diels–Alder adducts of 2- or 2,5-substituted furans and diethyl acetylenedicarboxylate is promoted by AlCl 3 in CH 2 Cl 2 at room temperature. The first adduct of 2,5-diphenylfuran to be isolated has been obtained from the same reaction at −20°. The aromatic compounds can be obtained alternatively by treating the adducts with BF 3 or H 2 SO 4 : where the adducts can be prepared by conventional means this two-step procedure has resulted in greatly improved yields. Adducts of furan and furfuryl alcohol are similarly converted to substituted phenols. HCl effected conversion only in the case of adducts carrying a bridgehead aryl substituent; in all other cases HCl added to the substituted double bond. The mechanism of the adduct rearrangement is discussed.

Furan

Furfuryl alcohol

Dimethyl acetylenedicarboxylate

10.1139/v69-716

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Citations (20)

Photochemistry of 1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene 2-carboxylate and 2,3-dicarboxylate esters

Canadian Journal of Chemistry (1977)

R. A. Matheson A. W. McCulloch A. G. McInnes David G. Smith

Direct irradiation (2537 Å) of methyl 1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene-2-carboxylate (13b) affords methyl 2,4-diphenyl-3-benzoxepine-1-carboxylate (17b) and methyl 1-benzoyl-3-phenylindene-2-carboxylate (19b), while acetone-sensitized irradiation yields chiefly 19b. The latter can be converted to methyl 3-phenylindene-2-carboxylate (21b).Direct irradiation of dimethyl 1,4-diphenyl-1,4-epoxy-1,4-dihydronaphthalene-2,3-dicarboxylate (13a) affords a mixture of dimethyl 2,4-diphenyl-3-benzoxepine-1,5-dicarboxylate (17a), dimethyl 1-benzoyl-3-phenylindene-1,2-dicarboxylate (19a), and dimethyl 1-benzoyl-2-phenylindene-1,3-dicarboxylate (18). The latter two products cleave readily to give dimethyl 3-phenylindene-1,2-dicarboxylate (21a) and dimethyl 2-phenylindene-1,3-dicarboxylate (20) respectively. Sensitized irradiation yields mainly 19a. The formation of 19a and 19b as major products of photorearrangement of 13a and 13b is consistent with a di-π-methane pathway producing methyl 4,6-diphenyl-5-oxatetracyclo[5.4.0.0. 2,4 0 3,6 ]undeca-1(7),8,10-triene 2-carboxylate and 2,3-dicarboxylate (25a,b), intermediates similar to those previously observed by other workers for benzonorbornadienes and 7-azabenzonorbornadienes. Compound 18 is derived by photo-induced rearrangement of the benzoxepine 17a.The AlCl 3 -catalyzed rearrangement of 13a yields a mixture of dimethyl 2,4-diphenyl-1(2H)-naphthalenone-2,3-dicarboxylate (15) and methyl 1,3-diphenyl-4-hydroxynaphthalene-2-carboxylate (16), while that of 13b affords only 16.

Carboxylate

10.1139/v77-197

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Citations (8)

ChemInform Abstract: EINFLUSS VON LEWIS‐SAEUREN AUF DIE DIELS‐ALDER‐RK. 4. MITT. RK. VON 2‐METHYL‐ UND 2‐PHENYL‐FURAN MIT AETHYL‐PROPIOLAT

Chemischer Informationsdienst (1972)

A. W. McCulloch A. G. McInnes

Abstract Die AlCl 3 ‐katalysierte Reaktion des Methyl‐furans (Ia) mit dem Propiolat (II) liefert den Ester (IIIa) (Hauptprodukt), viel polymerisiertes (Ia) und daneben sehr wenig der Verbindungen (IVa) (1 ,3% Ausbeute), (Va) (O,7%) und (VI) (0,2%).

Furan

10.1002/chin.197201223

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Citations (0)

ChemInform Abstract: THE REACTION OF PROPIOLIC ACID ESTERS WITH TERTIARY AMINES, FORMATION OF BETAINES

Chemischer Informationsdienst (1975)

A. W. McCulloch A. G. McInnes

Abstract Umsetzung des Propiolsäureesters (Ia) mit den Aminen (IIa)‐(IIc) bzw. des Propiolsäureesters (Ib) mit den Aminen (IIa) bzw. (IIc) in stark wäßrigem Medium führt zur Bildung entsprechender Betaine (III); als hauptsächliche Nebenprodukte werden ferner entsprechende trans‐Acrylate (IV) gebildet.

Betaine

Methyl acrylate

10.1002/chin.197505162

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Citations (0)

Synthesis of 6-Hydroxyfulvenes. II. Isomerization of 7-Oxanorbornadienes and 3-Oxaquadricyclanes

Canadian Journal of Chemistry (1975)

Raj K. Bansal A. W. McCulloch Paul W. Rasmussen A. G. McInnes

Substituted 7-oxanorbornadienes (1a–e) isomerize in good yield in the presence of iodine to 6-hydroxyfulvenes (2a–e): the reaction is catalyzed by light. Oxaquadricyclanes having bridgehead methyl substituents (3b, c) also undergo slow photoisomerization (2537 Å) to the same fulvenes. Irradiation of the oxanorbornadienes with bridgehead phenyl substituents (1d, e) resulted in oxepines (7d, e). Phenyl substituted oxaquadricyclanes could not be isolated.

Fulvenes

10.1139/v75-019

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Citations (13)

Applications of the ene reaction. Synthesis and properties of substituted α-methylene-γ-lactones

Canadian Journal of Chemistry (1981)

A. W. Hanson A. W. McCulloch A. G. McInnes

Substituted dimethyl 1,4-pentadiene-1,2-dicarboxylates (1 or 3) may be prepared by AlCl 3 -promoted or thermal ene reaction of olefins with dimethyl acetylenedicarboxylate. Lactonization of these adducts is catalyzed by acid. In the presence of 80% H 2 SO 4 the predominant product (ca. 80%) is a (Z)-dihydro-3-carbomethoxymethylene-2(3H)-furanone (2 or 4). Cyclization with anhydrous HCl affords a mixture of products, the composition of which depends on the starting material; major products include the corresponding (E)- and δ-lactone isomers (6 and 7). Detailed 1 H and 13 C nmr data are reported for all compounds. The structures of the (E)-4,5,5-trimethyl-, (Z)-4,5,5-trimethyl-, and (Z)-4,4,5,5-tetramethyl furanone derivatives (6a, 2a, and 2b) have been established by X-ray crystallography. The properties of some of these lactones are discussed, as are possible methods of removal of the carbomethoxyl from 2.

Ene reaction

Dimethyl acetylenedicarboxylate

Methylene

Anhydrous

10.1139/v81-047

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Citations (7)