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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 19
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Original Articles

Expeditious Synthesis of New 3,4,6‐Trihydroxythiepanes from d‐(‐)‐Quinic Acid

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Pages 3337-3349 | Received 10 Feb 2007, Published online: 05 Oct 2007

References

  • Chaveriat , L. , Stasik , I. , Demailly , G. and Beaupère , G. 2005 . First synthesis of 4,5‐O‐isopropylidene‐6‐thio‐D‐galactono‐1,6‐lactone as a precursor of d‐galactothioseptanose . Tetrahedron: Asymmetry , 16 : 623 – 627 .
  • Bozó , É. , Gáti , T. , Demeter , A. and Kuszmann , J. 2002 . Synthesis of 4‐cyano and 4‐nitrophenyl 1,6‐dithio‐d‐manno‐, l‐ido‐and d‐glucoseptanosides possessing antithrombotic activity . Carbohydr. Res. , 337 : 1351 – 1365 .
  • Halila , S. , Benazza , M. and Demailly , G. 2001 . Short and efficient synthesis of polyhydroxylated tetrahydrothiophene, tetrahydrothiopyrane and thiepane from bielectrophilic erythro, threo, xylo, ribo, arabino, manno and gluco α,ω‐dibromoalditol derivatives . Tetrahedron Lett. , 42 : 3307 – 3310 .
  • Le Merrer , Y. , Fuzier , M. , Dosbaa , I. , Foglietti , M.‐J. and Depezay , J.‐C. 1997 . Synthesis of thiosugars as weak inhibitors of glycosidases . Tetrahedron , 53 : 16731 – 16746 .
  • Fuzier , M. , Le Merrer , Y. and Depezay , J.‐C. 1995 . Thiosugars from d‐mannitol . Tetrahedron Lett. , 36 : 6443 – 6446 .
  • de Melo , E. B. , da Silveira Gomes , A. and Carvalho , I. 2006 . α‐and β‐Glycosidase inhibitors: Chemical structure and biological activity . Tetrahedron , 62 : 10277 – 10302 .
  • Yoshikawa , M. , Murakami , T. , Shimada , H. , Matsuda , H. , Yamahara , J. , Tanabe , G. and Muraoka , O. 1997 . Salacinol, potent antidiabetic principle with unique thiosugar sulfonium sulfate structure from the ayurvedic traditional medicine Salacia reticulata in Sri Lanka and India . Tetrahedron Lett. , 38 : 8367 – 8370 .
  • Johnston , B. D. , Jensen , H. H. and Pinto , B. M. 2006 . Synthesis of sulfonium sulfate analogues of disaccharides and their conversion to chain‐extended homologues of salacinol: New glycosidase inhibitors . J. Org. Chem. , 71 : 111 – 1118 . For representative synthesis and analogues, see
  • Ghavami , A. , Sadalapure , K. , Johnston , B. D. , Lobera , M. , Snider , B. B. and Pinto , B. M. 2003 . Improved syntheses of the naturally occurring glycosidase inhibitor salacinol . Synlett , : 1259 – 1262 .
  • Ghavami , A. , Johnston , B. D. and Pinto , B. M. 2001 . A new class of glycosidase inhibitor: Synthesis of salacinol and its stereoisomers . J. Org. Chem. , 66 : 2312 – 2317 .
  • Yoshikawa , M. , Murakami , T. , Yashiro , K. and Matsuda , H. 1998 . Kotalanol, a potent α‐glycosidase inhibitor with thiosugar sulfonium sulfate structure, from antidiabetic ayurvedic medicine Salacia reticulate . Chem. Pharm. Bull. , 46 : 1339 – 1340 .
  • Shih , T.-L. , Yang , B.-Y. , Li , S.-T. , Chiang , C.-F. and Lin , C.-H. 2007 . Expeditious synthesis of tri- and tetrahydroxyazepanes from D-(-)-quinic acid as potent glycosidase inhibitors . J. Org. Chem. , 72 : 4258 – 4261 .
  • Shih , T.‐L. , Lin , Y.‐L. and Kuo , W.‐S. 2005 . Highly stereoselective and stereospecific syntheses of a variety of quercitols from d‐(‐)‐quinic acid . Tetrahedron , 61 : 1919 – 1924 .
  • Plietker , B. and Miggemann , M. 2004 . The RuO4‐catalysed dihydroxylation, ketohydroxylation and mono oxidation‐novel oxidation reactions for the synthesis of diols and α‐hydroxy ketones . Org. Biomol. Chem. , 2 : 2403 – 2407 .
  • Shing , T. K. M. and Tam , E. K. W. 1998 . Enantiospecific syntheses of (+)‐crotepoxide, (+)‐boesenoxide, (+)‐β‐senepoxide, (+)‐pipoxide acetate, (‐)‐iso‐crotepoxide, (‐)‐senepoxide, and (‐)‐tingtanoxide from (‐)‐quinic acid . J. Org. Chem. , 63 : 1547 – 1554 .
  • Shing , T. K. M. , Tai , V. W.‐F. and Tam , E. K. W. 1994 . Practical and rapid vicinal hydroxylation of alkenes by catalytic ruthenium tetraoxide . Angew. Chem., Int. Ed. Engl. , 33 : 2312 – 2313 .
  • Cerè , V. , Pollicino , S. and Ricci , A. 2003 . New synthetic approach to enantiopure bicyclic sulfonium salts: Swainsonine analogues . J. Org. Chem. , 68 : 3311 – 3314 .

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