Abstract

Aritasone (1) A solution of pinocarvone (()-2) (100 mg, 0.66 mmol) in dichloromethane (5 mL) was pressurized to 19.9 kbar for 120 h. The 1H NMR spectrum of the crude reaction mixture showed significant change in the composition as compared to the starting material. The solvent was evaporated and the residue was purified by column chromatography (pentane/Et2O; 25/1) to afford aritasone (1) (20 mg, 40%) as a white solid; mp 101- 103 C; (lit3 mp 105-106 °C); []D 26 26.1 (c 0.40 in CHCl3); (lit3 []D 9 118); max/cm-1 (CHCl3) 2926, 2359, 1722, 1689, 1601, 1467, 1372, 1305, 1152; H (400 MHz; CDCl3, 298 K) 2.67 (2H, app dd, J 4.8, 2.5, H-2a, H-2b), 2.45-2.32 (3H, m, H-7a, H-15a, H-3), 2.15-2.01 (4H, m, H-10, H-12, H-15b, H-16a), 1.91-1.80 (2H, m, H-4, H-16b), 1.66 (1H, ddd, J 13.8, 6.4, 3.4, H-7b), 1.38 (3H, s, CH3), 1.29-1.22 (7H, br s, CH3, H-13a, H-13b, H-8a, H- 8b), 0.90 (3H, s, CH3), 0.80 (3H, s, CH3); C (100 MHz; CDCl3, 298 K) 209.5 (C), 142.9 (C), 112.8 (C), 80.8 (C), 45.2 (CH), 44.3 (CH), 43.7 (CH2), 40.9 (CH), 40.5 (C), 39.4 (CH), 38.3 (C), 33.2 (CH2), 32.7 (CH2), 27.7 (CH3), 27.3 (CH2), 27.3 (CH3), 26.3 (CH3), 22.5 (CH2), 22.1 (CH2), 20.9 (CH3); HRMS m/z (ES+ ) found 301.2162 (M + H) C20H29O2 requires 301.2162 and 323.1981 (M + Na) C20H28O2Na requires 323.1982. These data were consistent to those previously reported, 5, 7 however the value of the specific rotation5 differs significantly from that measured during the original isolation work.3

Christopher Hayes

Contact

• Room C16 School of Chemistry
  University Park
  Nottingham
  NG7 2RD
  UK
• 0115 951 3045
• 0115 951 3564
• chris.hayes@nottingham.ac.uk
• http://www.nottingham.ac.uk/~pczcjh/Homepage.html

Biography

Prof. Christopher Hayes began his academic career here in Nottingham with his B.Sc. in July 1992. Remaining at Nottingham, he completed his Ph.D. studies in organic chemistry, under the supervision of Professor Gerald Pattenden, in September 1995. In January 1996, on a NATO Postdoctoral Fellowship, he moved to the University of California at Berkeley where he worked in the group of Professor Clayton H. Heathcock. In September 1997, he returned to Nottingham as a Lecturer in Organic Chemistry, and has subsequently been promoted to Reader (2003), Associate Professor (2006) and Professor of Organic Chemistry (2011).

Research Summary

Research is centred in main-stream synthetic organic chemistry, focusing on the organic chemistry of biologically active molecules. His current research interests span a number of areas such as (i)… read more

Recent Publications

• NICOLLE, SIMON M., LEWIS, WILLIAM, HAYES, CHRISTOPHER J. and MOODY, CHRISTOPHER J., 2016. Stereoselective Synthesis of Functionalized Pyrrolidines by the Diverted N-H Insertion Reaction of Metallocarbenes with -Aminoketone Derivatives: Angewandte Chemie-International Edition Angewandte Chemie-International Edition. 55(11), 3749-3753
• BARTON, NAOMI A., MARSH, BENJAMIN J., LEWIS, WILLIAM, NARRAIDOO, NATHALIE, SEYMOUR, GRAHAM B., FRAY, RUPERT and HAYES, CHRISTOPHER J., 2016. Accessing low-oxidation state taxanes: is taxadiene-4(5)-epoxide on the taxol biosynthetic pathway?: Chemical Science Chemical Science. 7(5), 3102-3107
• PALFRAMAN, MATTHEW J., ALHARTHY, RIMA D., POWALOWSKA, PAULINA K. and HAYES, CHRISTOPHER J., 2016. Synthesis of triazole-linked morpholino oligonucleotides via Cu-I catalysed cycloaddition: Organic & Biomolecular Chemistry Organic & Biomolecular Chemistry. 14(11), 3112-3119
• NICOLLE, SIMON M., HAYES, CHRISTOPHER J. and MOODY, CHRISTOPHER J., 2015. Alkyl Halide-Free Heteroatom Alkylation and Epoxidation Facilitated by a Recyclable Polymer-Supported Oxidant for the In-Flow Preparation of Diazo Compounds: Chemistry-a European Journal Chemistry-a European Journal. 21(12), 4576-4579

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