Synthesis, Table of Contents SHORTPAPER© Georg Thieme Verlag Stuttgart · New YorkEffective Synthetic Routes to Cubylcarbinol DerivativesRonny 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(opens in new window) All articles of this category(opens in new window) 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 <A NAME="RM03702SS-1A">1a</A> Eaton PE. Cole TW. J. Am. Chem. Soc. 1964, 86: 962 <A NAME="RM03702SS-1B">1b</A> Eaton PE. Cole TW. J. Am. Chem. Soc. 1964, 86: 3157 <A NAME="RM03702SS-2A">2a</A> Service RF. Science 2000, 287: 564 <A NAME="RM03702SS-2B">2b</A> Zhang M.-X. Eaton PE. Gilardi R. Angew. Chem. Int. Ed. 2000, 39: 401 <A NAME="RM03702SS-2C">2c</A> Kortus J. Pederson MR. Richardson SL. Chem. Phys. Lett. 2000, 322: 224 <A NAME="RM03702SS-2D">2d</A> Hrovat DA. Borden WT. Eaton PE. Kahr B. J. Am. Chem. Soc. 2001, 123: 1289 <A NAME="RM03702SS-3A">3a</A> Eaton PE. Angew. Chem., Int. Ed. Engl. 1992, 31: 1421 <A NAME="RM03702SS-3B">3b</A> Mehrdad M. Sanjani NS. Polym. Int. 2000, 49: 260 <A NAME="RM03702SS-4">4</A> Cole TW. PhD Dissertation University of Chicago; USA: 1966. <A NAME="RM03702SS-5">5</A> Silverman RB. Zhou JP. Eaton PE. J. Am. Chem. Soc. 1993, 115: 8841 <A NAME="RM03702SS-6">6</A> Della EW. Hine PT. Patney HK. J. Org. Chem. 1977, 42: 2940 <A NAME="RM03702SS-7">7</A> 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 <A NAME="RM03702SS-8">8</A> Priefer R. Farrell PG. Harpp DN. Tetrahedron Lett. 2002, 43: in press <A NAME="RM03702SS-9A">9a</A> Eaton PE. Nordari N. Tsanaktsidis J. Upadhyaya SP. Synthesis 1995, 501 <A NAME="RM03702SS-9B">9b</A> Eaton PE. Yip YC. J. Am. Chem. Soc. 1991, 113: 7692 <A NAME="RM03702SS-10">10</A> Moriarty RM. Khosrowshahi JS. Dalecki TM. J. Chem. Soc., Chem. Commun. 1987, 675 <A NAME="RM03702SS-11">11</A> Eaton PE. Galoppini E. Gilardi R. J. Am Chem. Soc. 1994, 116: 7588 <A NAME="RM03702SS-12">12</A> Krishnamurthy S. Brown HC. J. Org. Chem. 1982, 47: 276 <A NAME="RM03702SS-13">13</A> Ashby EC. Welder CO. Doctorovich F. Tetrahedron Lett. 1993, 34: 7235 <A NAME="RM03702SS-14">14</A> Ashby EC. DePriest RN. Goel AB. Wenderoth B. Pham TN. J. Org. Chem. 1984, 49: 3545 <A NAME="RM03702SS-15">15</A> Luh T.-Y. Stock LM. J. Org. Chem. 1978, 43: 3271 <A NAME="RM03702SS-16">16</A> Della EW. Head NJ. J. Org. Chem. 1995, 60: 5303 <A NAME="RM03702SS-17A">17a</A> Eaton PE. Stossel D. J. Org. Chem. 1991, 56: 5138 <A NAME="RM03702SS-17B">17b</A> Eaton PE. Yang C.-X. Xiong Y. J. Am. Chem. Soc. 1990, 112: 3225 <A NAME="RM03702SS-18">18</A> Cole TW. Mayers CJ. Stock LM. J. Am. Chem. Soc. 1974, 96: 4555 <A NAME="RM03702SS-19">19</A> Edward JT. Farrell PG. Langford GE. J. Am. Chem. Soc. 1976, 98: 3075 <A NAME="RM03702SS-20">20</A> Moriarty RM. Khosrowshahi JS. Synth. Commun. 1989, 19: 1395 <A NAME="RM03702SS-21">21</A> 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.