Eurasian jays (Garrulus glandarius) show episodic-like memory through the incidental encoding of information.

Episodic memory describes the conscious reimagining of our memories and is often considered to be a uniquely human ability. As these phenomenological components are embedded within its definition, major issues arise when investigating the presence of episodic memory in non-human animals. Importantly, however, when we as humans recall a specific experience, we may remember details from that experience that were inconsequential to our needs, thoughts, or desires at that time. This 'incidental' information is nevertheless encoded automatically as part of the memory and is subsequently recalled within a holistic representation of the event. The incidental encoding and unexpected question paradigm represents this characteristic feature of human episodic memory and can be employed to investigate memory recall in non-human animals. However, without evidence for the associated phenomenology during recall, this type of memory is termed 'episodic-like memory'. Using this approach, we tested seven Eurasian jays (Garrulus glandarius) on their ability to use incidental visual information (associated with observed experimenter made 'caches') to solve an unexpected memory test. The birds performed above chance levels, suggesting that Eurasian jays can encode, retain, recall, and access incidental visual information within a remembered event, which is an ability indicative of episodic memory in humans.

Episodic-like memory in wild free-living blue tits and great tits.

Episodic-like memory in non-human animals represents the behavioral characteristics of human episodic memory-the ability to mentally travel backward in time to "re-live" past experiences. A focus on traditional model species of episodic-like memory may overlook taxa possessing this cognitive ability and consequently its evolution across species. Experiments conducted in the wild have the potential to broaden the scope of episodic-like memory research under the natural conditions in which they evolved. We combine two distinct yet complementary episodic-like memory tasks (the what-where-when memory and incidental encoding paradigms), each targeting a different aspect of human episodic memory, namely the content (what-where-when) and process (incidental encoding), to comprehensively test the memory abilities of wild, free-living, non-caching blue tits (Cyanistes caeruleus) and great tits (Parus major). Automated feeders with custom-built programs allowed for experimental manipulation of spatiotemporal experiences on an individual-level basis. In the what-where-when memory experiment, after learning individualized temporal feeder rules, the birds demonstrated their ability to recall the "what" (food type), "where" (feeder location), and "when" (time since their initial visit of the day) of previous foraging experiences. In the incidental encoding experiment, the birds showed that they were able to encode and recall incidental spatial information regarding previous foraging experiences ("where" test), and juveniles, but not adults, were also able to recall incidentally encoded visual information ("which" test). Consequently, this study presents multiple lines of converging evidence for episodic-like memory in a wild population of generalist foragers, suggesting that episodic-like memory may be more taxonomically widespread than previously assumed.

Bottlenose dolphins are sensitive to human attentional features, including eye functionality.

The ability to attribute attentional states to other individuals is a highly adaptive socio-cognitive skill and thus may have evolved in many social species. However, whilst humans excel in this ability, even chimpanzees appear to not accurately understand how visual attention works, particularly in regard to the function of eyes. The complex socio-ecological background and socio-cognitive skill-set of bottlenose dolphins (Tursiops sp.), alongside the specialised training that captive dolphins typically undergo, make them an especially relevant candidate for an investigation into their sensitivity to human attentional states. Therefore, we tested 8 bottlenose dolphins on an object retrieval task. The dolphins were instructed to fetch an object by a trainer under various attentional state conditions involving the trainer's eyes and face orientation: 'not looking', 'half looking', 'eyes open', and 'eyes closed'. As the dolphins showed an increased latency to retrieve the object in conditions where the trainer's head and eyes cued a lack of attention to the dolphin, particularly when comparing 'eyes open' vs 'eyes closed' conditions, we demonstrate that dolphins can be sensitive to human attentional features, namely the functionality of eyes. This study supports growing evidence that dolphins possess highly complex cognitive abilities, particularly those in the social domain.

Social influences on delayed gratification in New Caledonian crows and Eurasian jays.

Self-control underlies goal-directed behaviour in humans and other animals. Delayed gratification - a measure of self-control - requires the ability to tolerate delays and/or invest more effort to obtain a reward of higher value over one of lower value, such as food or mates. Social context, in particular, the presence of competitors, may influence delayed gratification. We adapted the 'rotating-tray' paradigm, where subjects need to forgo an immediate, lower-quality (i.e. less preferred) reward for a delayed, higher-quality (i.e. more preferred) one, to test social influences on delayed gratification in two corvid species: New Caledonian crows and Eurasian jays. We compared choices for immediate vs. delayed rewards while alone, in the presence of a competitive conspecific and in the presence of a non-competitive conspecific. We predicted that, given the increased risk of losing a reward with a competitor present, both species would similarly, flexibly alter their choices in the presence of a conspecific compared to when alone. We found that species differed: jays were more likely to select the immediate, less preferred reward than the crows. We also found that jays were more likely to select the immediate, less preferred reward when a competitor or non-competitor was present than when alone, or when a competitor was present compared to a non-competitor, while the crows selected the delayed, highly preferred reward irrespective of social presence. We discuss our findings in relation to species differences in socio-ecological factors related to adult sociality and food-caching (storing). New Caledonian crows are more socially tolerant and moderate cachers, while Eurasian jays are highly territorial and intense cachers that may have evolved under the social context of cache pilfering and cache protection strategies. Therefore, flexibility (or inflexibility) in delay of gratification under different social contexts may relate to the species' social tolerance and related risk of competition.

Episodic-like memory in common bottlenose dolphins.

Episodic memory involves the conscious recollection of personally experienced events, which has often been argued to be a uniquely human ability.1-5 However, evidence for conscious episodic recall in humans is centered around language-based reports. With no agreed upon non-linguistic behavioral makers of consciousness,6 episodic-like memory7 therefore represents the behavioral characteristics of human episodic memory, in the absence of evidence for subjective experience during recall. Here, we provide compelling evidence for episodic-like memory in common bottlenose dolphins (Tursiops truncatus), based on the incidental encoding and unexpected question paradigm.8 This methodology aims to capture the incidental encoding characteristic of human episodic memory, in that when we recall an experience, we remember information that was trivial at the time of encoding, but was encoded automatically.9 We show that dolphins are able to use incidentally encoded spatial ("where") and social ("who") information to solve an unexpected memory task, using only a single test trial per test type, which ensured that the dolphins did not have the opportunity to semantically learn "rules" to pass the test. All participating dolphins made correct choices in both the "where" and "who" tests. These results suggest that dolphins are capable of encoding, recalling, and accessing incidental information within remembered events, which is an ability indicative of episodic memory in humans. We argue that the complex socio-ecological background of dolphins may have selected for the ability to recall both spatial and social information in an episodic-like manner.

Progress toward the total synthesis of psymberin/irciniastatin A.

In this paper, we describe our synthesis of four key building blocks for the total synthesis of psymberin (1) and its C4 epimer (2). Despite early difficulties in processing material to the advanced intermediate stage, we have been successful in developing high-yielding syntheses for the pyran core, natural side chain, 4-epi side chain, and aryl fragments of the molecule. Our findings from the optimization process are presented herein.

Delayed recurrence of renal cell carcinoma presenting as a haemorrhoid.

Metastatic non-colorectal cancer of the anal canal is a rare entity. To date, only four cases have been described in the literature. We present a 76-year-old man who was referred with an unusual perianal lesion. He had a history of renal cell carcinoma 7 years previously. Histologically, the lesion revealed clear cell carcinoma in keeping with metastasis. To our knowledge, this is only the second time a renal carcinoma metastasis to the anal canal has been identified.

Oxidative rearrangement of indoles: a new approach to the EFHG-tetracyclic core of diazonamide A.

A new approach to the ring EFHG-tetracyclic core fragment of the marine secondary metabolite diazonamide A is described. The route is based on the oxidative rearrangement of 3-arylindole-2-carboxylates. Thus, a range of 3-arylindole-2-carboxylates (3, 8) underwent rearrangement to the corresponding 3,3-disubstituted oxindoles (4, 9) with migration of the ester group upon treatment with tert-butyl hypochlorite followed by acid. The oxindoles 9 with a 3-[2-(4-methoxybenzyloxy)]phenyl substituent underwent cyclization to the tetracyclic aminals 11 following N-protection, reduction, and treatment with methanesulfonic anhydride. The methodology was applied to the tyrosine-indole derivative 17 to give the EFHG-tetracyclic core of diazonamide A.

The diazo route to diazonamide A. Studies on the indole bis-oxazole fragment.

[structure: see text] Various approaches to the indole bis-oxazole fragment of the marine secondary metabolite diazonamide A are described, all of which feature dirhodium(II)-catalyzed reactions of diazocarbonyl compounds in key steps. Thus, 3-bromophenylacetaldehyde is converted into an alpha-diazo-beta-ketoester, dirhodium(II)-catalyzed reaction of which with N-Boc-valinamide resulted in N-H insertion of the intermediate rhodium carbene to give a ketoamide that readily underwent cyclodehydration to give (S)-2-(1-tert-butoxycarbonylamino)-2-methylpropyl]-5-(3-bromobenzyl)oxazole-4-carboxamide, after ammonolysis of the initially formed ester. This aryl bromide was then coupled to a 3-formyl-indole-4-boronate under Pd catalysis to give the expected biaryl. Subsequent conversion of the aldehyde group into a second alpha-diazo-beta-ketoester gave a substrate for an intramolecular carbene N-H insertion, although attempts to effect this cyclization were unsuccessful. A second approach to an indole bis-oxazole involved an intermolecular rhodium carbene N-H insertion, followed by oxazole formation to give (S)-2-[1-tert-(butoxycarbonylamino)-2-methylpropyl]-5-methyloxazole-4-carboxamide. A further N-H insertion of this carboxmide with the rhodium carbene derived from ethyl 2-diazo-3-[1-(2-nitrobenzenesulfonyl)indol-3-yl]-3-oxopropanoate gave a ketoamide, cyclodehydration of which gave the desired indole bis-oxazole. Finally, the boronate formed from 4-bromotryptamine was coupled to another diazocarbonyl-derived oxazole to give the corresponding biaryl, deprotection and cyclization of which produced a macrocyclic indole-oxazole derivative. Subsequent oxidation and cyclodehydration incorporated the second oxazole and gave the macrocyclic indole bis-oxazole.

Control of competing N-H insertion and Wolff rearrangement in dirhodium(II)-catalyzed reactions of 3-indolyl diazoketoesters. synthesis of a potential precursor to the marine 5-(3-indolyl)oxazole martefragin A.

Dirhodium(II)-catalyzed reaction of 3-indolyl alpha-diazo-beta-ketoester 25 in the presence of hexanamide results in competing metal carbene N-H insertion and Wolff rearrangement. The corresponding phenyl diazoketoester 32, on the other hand, gives only the product of N-H insertion, suggesting that the indole moiety is more prone to 1,2-rearrangement. The competing processes were investigated in a range of 3-indolyl alpha-diazo-beta-ketoesters (36, 38, 40, 44); these studies established that the Wolff rearrangement could be effectively suppressed by the presence of a strong electron-withdrawing group on the indole nitrogen. Dirhodium(II) catalysts were also more effective than copper or Lewis acid catalysts in favoring the insertion process. The products of N-H insertion, the ketoamides (26, 47, 49, 51, 53), were readily cyclodehydrated to the corresponding 5-(3-indolyl)oxazoles. The N-H insertion/cyclodehydration methodology was used in a formal synthesis of the marine natural product martefragin A. Thus the N-Boc homoisoleucine amide 23, prepared by asymmetric hydrogenation of a dehydro amino acid, underwent N-H insertion with the rhodium carbene derived from the N-nosyl indolyl diazoester 40, followed by cyclodehydration and deprotection to give the 5-(3-indolyl)oxazole martefragin A precursor 75.