Synthesis of 4‐Octuloses. Part 6. 4‐Octulose Derivatives, Prepared from L‐Sorbose, as Key Intermediates in the Stereoselective Synthesis of C‐Glycoside and Polyhydroxyindolizidine Analogues.
Reactions of 1 and 12 with p-toluenesulfonyl chloride in pyridine gave the corresponding 1-O-p-toluenesulfonyl derivatives 2 and 13 in yields of 91% and 60%, respectively. Compound 12 was also transformed into 14 by treatment with I2/ Ph3P/imidazole in anhydrous dichloromethane. Treatment of compounds 12 and 13/14 with NaN3 in DMF furnished the respective 1-azido-1-deoxy derivatives 3 and 15, which were then deacetonated to give the free 4-octuloses 4 and 16. These were subsequently hydrogenated in the presence of 10% Pd/C to afford the expected polyhydroxylated branched-chain pyrrolidines 5 and 17. Attempted OH R
4‐Octulose Derivatives, Prepared from L‐Sorbose, as Key Intermediates in the Stereoselective Synthesis of C‐Glycoside and Polyhydroxyindolizidine Analogues
Reactions of 1 and 12 with p-toluenesulfonyl chloride in pyridine gave the corresponding 1-O-p-toluenesulfonyl derivatives 2 and 13 in yields of 91% and 60%, respectively. Compound 12 was also transformed into 14 by treatment with I2/Ph3P/imidazole in anhydrous dichloromethane. Treatment of compounds 12 and 13/14 with NaN3 in DMF furnished the respective 1-azido-1-deoxy derivatives 3 and 15, which were then deacetonated to give the free 4-octuloses 4 and 16. These were subsequently hydrogenated in the presence of 10% Pd/C to afford the expected polyhydroxylated branched-chain pyrrolidines 5 and 17. Attempted OH OMes transformation at C-8 in the N−Cbz-protected pyrrolidines 7 and 19 was unsuccessful and an internal anhydration process took place to yield the corresponding C-glycoside-like furanoses 9 and 20. On the other hand, 23 was transformed into the D-ribo analogue 25 through reduction of the intermediate 4,6-diulose 24. Finally, deprotection of 25 in acid medium to give the free 4-ulose 26, followed by hydrogenation of the latter in the presence of 10% Pd/C in methanol, allowed the preparation of (6S,7S,8S,8aS)-6,7,8-trihydroxy-8a-methoxyindolizidin-3-one (27).
Medieval Modal Theories and Modal Logic Handbook of the History of Logic. Volume 2: Mediaeval and Renaissance Logic
1The translation of the Categories is edited by L. Minio-Paluello in Aristoteles Latinus 1.1-5 (Bruges-Paris: Descl~e de Brouwer, 1961) and the translation of the De interpretatione by L. Minio-Paluello in Aristoteles Latinus II.1-2 (Bruges-Paris: Descl~e de Brouwer, 1965). The translation of Porphyry's Isagoge is edited by L. Minio-Paluello and B.G. Dod in Aristoteles Latinus 1.6-7 (Bruges-Paris: Descl~e de Brouwer, 1966). Boethius's commentary on Aristotle's Categories is found in Patrologia Latina (ed. J.-P. Migne), 64, 159-294, De syllogismis categoricis in Patrologia Latina 64, 793-832, In Ciceronis Topica in Patrologia Latina 64, 1039-1169; an English translation with notes and an introduction by E. Stump, and De differentiis topicis in Patrologia Latina 64, 1174-1216; an English translation with notes and essays by E. Stump, Boethius's De topicis differentiis (Ithaca and London: Cornell University Press, 1978), Boethius's In Ciceronis Topica (Ithaca and London: Cornell University Press, 1988). Boethius's two commentaries on De interpretatione are edited by C. Meiser (Leipzig: Teubner, 1877-1880), his two commentaries on Porphyry's Isagoge by S. Brandt, Corpus Scriptorum Ecclesiasticorum Latinorum 48 (Leipzig: G. Freytag, Vienna: F.Tempsky, 1906), De hypotheticis syllogismis by L. Obertello (Brescia: Paideia, 1969) and De divisione by J. Magee, with a translation and commentary (Leiden: Brill, 1998). Some other ancient works were also used, such as Apuleius's Peri hermeneias (ed. C. Moreschini in Opera III (Stuttgart: Teubner, 1991), Augustine's Dialectica, trans, with notes by B.D. Jackson from the text edited by J. Pinborg, Synthese Historical Library 16 (Dordrecht: Reidel, 1975), and pseudo-Augustinean De decern categoriis, ed. L. Minio-Paluello, in Aristoteles Latinus 1.1-5, 133-75. For the sources of eleventh and twelfth century logic, see J. Marenbon, 'Medieval Latin Commentaries and Glosses on Aristotelian Logical Texts, Before c. 1150 AD' in Ch. Burnett (ed.), Glosses and Commentaries on Aristotelian Logical Tezts (Warburg Institute Surveys and Texts 23), (London: Warburg Institute, 1993), 77-127, republished and revised in J. Marenbon, Aristotelian Logic, Platonism, and the Contezt of Early Medieval Philosophy in the West, Variorum Collected Studies Series (Aldershot: Ashgate, 2000). 2Analytica priora, ed. L. Minio-Paluello, Aristoteles Latinus III.l-4 (Bruges-Paris: Descl~e de Brouwer, 1962), Analytica posteriora, ed. L. Minio-Paluello and B.G. Dod, Aristoteles Latinns IV.l-4 (Bruges-Paris: Descl~e de Brouwer, 1968), Topica, ed. L. Minio-Paluello and B.G.