Carbanucleosides: synthesis of both enantiomers of 2-(6-chloro-purin-9-yl)-3,5-bishydroxymethyl cyclopentanol from D-glucose

The key intermediate 1,2:5,6-di-O-isopropylidene-3-deoxy-3 beta-allyl-alpha-D-glucofuranose (8) could be conveniently prepared through radical induced allyl substitution at C-3 of appropriate 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose derivatives (7a,b) and used to synthesize enantiomeric bishydroxymethyl aminocyclopentanols 13 and 19 by the application of a 1,3-dipolar nitrone cycloaddition reaction involving the C-5 or C-1 aldehyde functionality. The products were subsequently transformed into carbanucleoside enantiomers 15 and 21. The diastercomeric isoxazolidinocyclopentane derivative 20 was similarly converted to carbanucleoside 22. (c) 2006 Elsevier Ltd. All rights reserved.

Synthesis of oxepane ring containing monocyclic, conformationally restricted bicyclic and spirocyclic nucleosides from d-glucose: a cycloaddition approach

Carbohydrate-derived substrates having (i) C-5 nitrone and C-3-O-allyl, (ii) C-4 vinyl and a C-3-O-tethered nitrone, and (iii) C-5 nitrone and C-4-allyloxymethyl generated tetracyclic isoxazolidinooxepane/-pyrart ring systems upon intramolecular nitrone cycloaddition reactions. Deprotection of the 1,2acetonides of these derivatives followed by introduction of uracil base via Vorbruggen reaction condition and cleavage of the isooxazolidine rings as well as of benzyl groups by transfer hydrogenolysis yielded an oxepane ring containing blicyclic and spirocyclic nucleosides. The corresponding oxepane based nucleoside analogues were prepared by cleavage of isoxazolidine and furanose rings, coupling of the generated amino functiontalities with 5-amino-4,6-dichloropyrimidine, cyclization to purine rings, and finally aminolysis.

‘The Making of the Book’: Roy Fisher, the Circle Press and the poetics of book art

Between 1972 and 2001, the English late-modernist poet Roy Fisher provided the text for nine separate artist's books produced by Ron King at the Circle Press. Taken together, as Andrew Lambirth has written, the Fisher-King collaborations represent a sustained investigation of the various ways in which text and image can be integrated, breaking the mould of the codex or folio edition, and turning the book into a sculptural object. From the three-dimensional pop-up designs of Bluebeard's Castle (1973), each representing a part of the edifice (the portcullis, the armoury and so on), to ‘alphabet books’ such as The Half-Year Letters (1983), held in an ingenious french-folded concertina which can be stretched to over a metre long or compacted to a pocketbook, the project of these art books is to complicate their own bibliographic codes, and rethink what a book can be. Their folds and reduplications give a material form to the processes by which meanings are produced: from the discovery, in Top Down, Bottom Up (1990), of how to draw on both sides of the page at the same time, to the developments of The Left-Handed Punch (1987) and Anansi Company (1992), where the book becomes first a four-dimensional theatre space, in which a new version of Punch and Judy is played out by twelve articulated puppets, and then a location for characters that are self-contained and removable, in the form of thirteen hand-made wire and card rod-puppets. Finally, in Tabernacle (2001), a seven-drawer black wooden cabinet that stands foursquare like a sculpture (and sells to galleries and collectors for over three thousand pounds), the conception of the book and the material history of print are fully undone and reconstituted. This paper analyses how the King-Fisher art books work out their radically material poetics of the book; how their emphasis on collaboration, between artist and poet, image and text, and also book and reader – the construction of meaning becoming a co-implicated process – continuously challenges hierarchies and fixities in our conception of authorship; and how they re-think the status of poetic text and the construction of the book as material object.