Synthesis, Table of Contents SHORTPAPER © Georg Thieme Verlag Stuttgart · New York Effective Synthetic Routes to Cubylcarbinol Derivatives Ronny Priefer, Patrick G. Farrell, David N. Harpp*Department of Chemistry, McGill University, Montreal, Quebec, H3A 2K6, Canadae-Mail: david.harpp@mcgill.ca; Recommend Article Abstract Buy Article All articles of this category Abstract Three alternative routes for the synthesis of cubylcarbinol (1) from 4-iodocubanecarboxylic acid (5) are described. Key words cubane derivatives - 4-iodocubylcarbinol - cubylcarbinol - iodine removal Full Text References References 1a Eaton PE. Cole TW. J. Am. Chem. Soc. 1964, 86: 962 1b Eaton PE. Cole TW. J. Am. Chem. Soc. 1964, 86: 3157 2a Service RF. Science 2000, 287: 564 2b Zhang M.-X. Eaton PE. Gilardi R. Angew. Chem. Int. Ed. 2000, 39: 401 2c Kortus J. Pederson MR. Richardson SL. Chem. Phys. Lett. 2000, 322: 224 2d Hrovat DA. Borden WT. Eaton PE. Kahr B. J. Am. Chem. Soc. 2001, 123: 1289 3a Eaton PE. Angew. Chem., Int. Ed. Engl. 1992, 31: 1421 3b Mehrdad M. Sanjani NS. Polym. Int. 2000, 49: 260 4 Cole TW. PhD Dissertation University of Chicago; USA: 1966. 5 Silverman RB. Zhou JP. Eaton PE. J. Am. Chem. Soc. 1993, 115: 8841 6 Della EW. Hine PT. Patney HK. J. Org. Chem. 1977, 42: 2940 7 Priefer R. Lee YJ. Barrios F. Wosnick JH. Lebuis A.-M. Farrell PG. Harpp DN. Sun A. Wu S. Snyder JP. J. Am. Chem. Soc. 2002, 124: 5626 8 Priefer R. Farrell PG. Harpp DN. Tetrahedron Lett. 2002, 43: in press 9a Eaton PE. Nordari N. Tsanaktsidis J. Upadhyaya SP. Synthesis 1995, 501 9b Eaton PE. Yip YC. J. Am. Chem. Soc. 1991, 113: 7692 10 Moriarty RM. Khosrowshahi JS. Dalecki TM. J. Chem. Soc., Chem. Commun. 1987, 675 11 Eaton PE. Galoppini E. Gilardi R. J. Am Chem. Soc. 1994, 116: 7588 12 Krishnamurthy S. Brown HC. J. Org. Chem. 1982, 47: 276 13 Ashby EC. Welder CO. Doctorovich F. Tetrahedron Lett. 1993, 34: 7235 14 Ashby EC. DePriest RN. Goel AB. Wenderoth B. Pham TN. J. Org. Chem. 1984, 49: 3545 15 Luh T.-Y. Stock LM. J. Org. Chem. 1978, 43: 3271 16 Della EW. Head NJ. J. Org. Chem. 1995, 60: 5303 17a Eaton PE. Stossel D. J. Org. Chem. 1991, 56: 5138 17b Eaton PE. Yang C.-X. Xiong Y. J. Am. Chem. Soc. 1990, 112: 3225 18 Cole TW. Mayers CJ. Stock LM. J. Am. Chem. Soc. 1974, 96: 4555 19 Edward JT. Farrell PG. Langford GE. J. Am. Chem. Soc. 1976, 98: 3075 20 Moriarty RM. Khosrowshahi JS. Synth. Commun. 1989, 19: 1395 21 Instead of preparing the anhyd sodium salt of N-hydroxypyridine-2-thione from sodium omadine, we used commercially available 2-mercaptopyridine-N-oxide sodium salt hydrate.
