The Synthesis of Dihydrocitrinin and Citrinin

Warren, Harold H.; Dougherty, Gregg; Wallis, Everett S.

doi:10.1021/ja01178a047

Cited by 16 publications

(8 citation statements)

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“…of short-nosed bandicoots, J. macrourus, from Innisfail suggests that, although rodents constitute the main reservoirs, infection may at times extend to the other small mammals of the same habitat. Previously, Warren et al (1949) had found no evidence of infection in 10 species of small wild mammals other than rats, and it appears, from the results recorded here, that there is little, if any, overflow of infection from rats to cats and dogs in Brisbane.…”

Section: Resultssupporting

confidence: 47%

A Survey for Antibodies to Encephalomyocarditis Virus in Man and Animals

Pope

Scott

1960

Aust J Exp Biol Med

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Neutralizing antibodies to the Innisfail strain of EMC virus were present at significant levels, in one of 337 human sera collected in Queensland, and in one of 48 from Papua.Antibodies were also present, in Queensland, in 22 p.c. of water-rats, Hydromys chrysogaster; in 5-10 p.c. of rats, Rattus rattus, R. norvegicus, R. sordidus conatus and Melomys lutillus littoralis; in 2 p.c. of bandicoots, Isoodon macrourus; and in one of 44 horses. A series of mice, cats, dogs and kangaroos examined was negative.

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Section: Resultssupporting

confidence: 47%

A Survey for Antibodies to Encephalomyocarditis Virus in Man and Animals

Pope

Scott

1960

Aust J Exp Biol Med

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“…The procedure was later extended to citrinin and dihydrocitrinin analogs by the use of different aldehydes, ketones and acetals. [16] Crude yields were 50-80 %. At the beginning of the 1970s, Micheel and Schleifstein described the cyclocondensation of benzene and glyceraldehyde in liquid hydrogen fluoride to furnish l-(1Ј,2Ј-dihydroxyethyl)-3-hydroxymethyl-4-phenylisochroman in 35-40 % yield.…”

Section: Early Applications Of the Oxa-pictet-spengler Cyclizationmentioning

confidence: 97%

“…The reaction conditions were optimized (Table 7) for the cyclocondensation of 3-methoxybenzaldehyde with 2-(3,4-dimethoxyphenyl)ethanol (16), and TsOH was found to be the best promoter. Employing an activated β-phenethyl alcohol, yields were above 80 % (Table 8); however, in case of substrates like β-phenethyl alcohol itself, with no activating substituents on the phenyl ring, the reaction did not take place to an appreciable extent; therefore, β-phenethyl alcohols with electron-withdrawing groups are not expected to react under these conditions.…”

Section: New Promoters Of the Oxa-pictet-spengler Cyclizationmentioning

confidence: 99%

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

2011

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The oxa‐Pictet–Spengler cyclization is the oxygen variation of the Pictet–Spengler reaction, in which an aromatic alcohol component (generally a β‐arylethyl alcohol) reacts with acarbonyl component (aldehyde, ketone or their masked derivatives), to yield a 1‐substituted (or 1,1′‐disubstituted)pyran fused to the aromatic ring system found in the starting alcohol. The transformation is usually promoted by Brønsted and Lewis acids. Intramolecular versions of the reaction are also known, where both components are mutually masked as an acetal. Discussed here are aspects concerning the most recent developments and new applications of this useful reaction, including the scope and limitations of new promoters, and new mechanistic pictures of this transformation. The use of novel stereochemical control strategies and the application of the reaction to the synthesis of natural products and their analogs, as well as to accessing fully synthetic bioactive compounds and new ring systems are presented, and chiral versions of the oxa‐Pictet–Spengler are also analyzed.

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“…The method of preparing complement fixing antigen employed by Warren, Smadel and Russ (1949) proved suitable for use with the Innisfail strain, but not with the EMC strain. Consequently antigens for both strains were prepared from the brains of suckling miee, rather than of weaned mice, and proved quite effective.…”

Section: Methodsmentioning

confidence: 99%

A VIRUS OF THE ENCEPHALOMYOCARDITIS GROUP FROM A WATER‐RAT, HYDROMYS CHRYSOGASTER, IN NORTH QUEENSLAND

Pope

1959

Aust J Exp Biol Med

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A virus, referred to as the Innisfail strain, was isolated by mouse inoculation horn a naturally Infected water-rat, Hydromys chrysogaster, captured in north Queensland, Australia. It was shown to be indistinguishable from the EMC vims of Helwig and Schmidt by cross-neutralization and cross-complement fixation tests, and was considered to belong to the EMC group of viruses.Mice and guinea-pigs were highly susceptible. Rats showed signs of paralysis, but usually survived. Rabbits and three-day-old chickens were resistant.Infection of mice was characterised by paralysis and death in 2-3 days, and encephalitis and myositis were the prominent histopathological features. Heavily infected guinea-pigs died within 3-7 days, with encephalitis and seveie macroscopic myocarditis. This is believed to be the first report of natural infection with a virus of the EMC group in Australia.Toxoplasma was also isolated from the water-rat, making a new host record.

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The Synthesis of Dihydrocitrinin and Citrinin

Cited by 16 publications

References 0 publications

A Survey for Antibodies to Encephalomyocarditis Virus in Man and Animals

A Survey for Antibodies to Encephalomyocarditis Virus in Man and Animals

Synthesis of Oxacycles Employing the Oxa‐Pictet–Spengler Reaction: Recent Developments and New Prospects

A VIRUS OF THE ENCEPHALOMYOCARDITIS GROUP FROM A WATER‐RAT, HYDROMYS CHRYSOGASTER, IN NORTH QUEENSLAND

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