References and Notes
- Massiot , G. and Delaude , C. 1986 . in The Alkaloids , Edited by: Manske , R. H. F. Vol. 27 , New York : Academic Press . Chapter 3
- Padwa , A. and Norman , B. H. 1990 . J. Org. Chem. , 55 : 4081
- Wang , C. J. and Wuonola , M. A. 1990 . Org. Prep. Rep. , : 447
- Jorids , U. , Sauter , F. , Siddiqi , S. M. , Kuenburg , B. and Bhattacharya , K. 1990 . Synthesis , : 925
- Lee , J. W. , Son , H. J. , Lee , J. H. , Jung , E. Y. , Yoon , G. J. and Park , M. H. Synth. Commun. , in press.
- Lee , J. W. , Son , H. J. and Choi , M. J. 1994 . Korean J. Med. Chem. , 4 : 119
- The chlorination of hydroxy group using methanesulfonyl chloride in CH2Cl2 in the presence of Et3N is carried out by the mesylation of hydroxy group followed chlorine anion attack to the intermediate generated from the anchimeric assistance of SCH3 group.
- Greene , T. W. and Wuts , P. G.M. 1991 . Protective Groups in Organic Synthesis, , 2nd Ed. , John Wiley and Sons, Inc. .
- Ishibashi , H. , Harada , S. , Okada , M. , Somekawa , M. , Kido , M. and Ikeda , M. 1989 . Chem. Pharm. Bull. , 37 : 939
- Lee , J. W. , Lee , J. H. , Son , H. J. , Choi , Y. K. , Yoon , G. J. and Park , M. H. Synth. Commun. , submitted.
- Agami , C. , Couty , F. , Hamon , L. and Venier , O. 1993 . Tetrahedron Lett. , 34 : 4509
- The preparation of compound 5 from compound 3 is as follows: To a stirred solution of 3 (0.34 g, 0.87 mmol) in 6 ml of THF was added dropwise 0.6 ml (0.95 mmol) of n-BuLi (1.6M in hexane) at 0°C. After stirring for 30 min at 0°C, a solution of TsCl (0.17 g, 0.87 mmol) in 2 ml of THF was added dropwise at 0°C and stirred at 0°C for 1h. To the resulting solution was added dropwise 1.9 ml(1.74 mmol) of t-BuOK (1M in THF) at 0°C. The mixture was stirred at 0°C for 30 min, treated with saturated ammonium chloride solution, and extracted with chloroform. The organic layer was dried and concentrated. The residue was chromatographed on silicagel eluting EtOAc as an eluent to give 0.11 g (37%) of 5: mp 93∼96°C; 1HNMR (CDCl3) δ 1.46(s, 18H), 1.93∼2.26(m, 2H), 2.46 and 2.48(two s, 3H), 3.32∼3.97(m, 6H), 4.38∼4.63(m, 1H); MS(70ev), m/z(%) 57(base peak), 310(M+ - 64, loss of CH3S(O)H).
- 6: 1HNMR (CDCl3) δ 1.46(s, 18H), 2.12(s, 3H), 2.00∼2.16(m, 2H), 3.35∼3.69(m, 6H), 4.06(m, 1H); MS(70ev), m/z(%) 57(base peak), 358(M+). 7: mp 142∼145°C; 1HNMR (DMSO-d6) δ 2.19(s, 3H), 2.08∼2.38(m, 2H), 3.25∼3.85(m, 6H), 4.06∼4.22(m, 1H). 13: mp 109∼111°C; 1HNMR (DMSO-d6) δ 2.21(s, 3H), 2.25∼2.36(m, 2H), 2.64(s, 3H), 3.20∼3.42(m, 3H), 3.93∼4.20(m, 4H).