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1 15.1 5~10 C 76~86% R.A. Pacaud< C.F.. Allen, rg. Synth., Coll. Vol. 2, 336 (1943). C C 2 C 2 3 Si C 2 C 2 98% P. Boudjouk, B.-K. Kim, B.-. an, J. Chem. Educ., 74, 1223 (1997). ( ) 3 CC C 2 Ac ( ) 3 CC ( ) 2 CC( ) 2 1,2-!"#$% ( ) 3 CC Ac ( ) 3 CC ( ) 2 CC( ) 2 35~40% 15~20% 40~50% R. C. Fahey, C. A. Mcerson, J. Am. Chem. Soc., 91, 3865 (1969). KI, 3 P 4 80 C, 3 h 88~90% I. Stone,. Shechter, rg. Synth., Coll. Vol. 4, 543 (1963). R. 2 74~79% C 2 G.F. Woods, rg. Synth., Coll. Vol. 3, 470 (1955).

2 C 3 BF 3 Et 2, 3 P 4 C % androstanolone R.E. Ireland, T.. 'Neil, G.L. Tolman, rg. Synth., Coll. Vol. 7, 66 (1990). Ts 78~92% C 2 C 2 1) EtMg 2) C 2 / 60~65% R. A. Earl, L. B. Townsend, rg. Synth., Coll. Vol. 7, 334(1990). h!, 2 S 4 52~53% ()-limonene!"#$%&'()*,-./ F.P. Tise, P.J. Kropp, rg. Synth., Coll. Vol. 7, 304 (1990). RC 2 C C 2 C 2 C 2 2 S 4 C 2 C( ) 3 C 2 C( ) 3 A. L. Mcoskey, et al., rg. Synth., Coll. Vol. 4, 261(1963).

3 C 2 (exo)! 90.5~92.5% D. C. Kleinfelter, P. von R. Schleyer, rg. Synth., Coll. Vol. 5, 852 (1973). BF 3 Et 2 Ac Ac ( ca. 90 : 10 ) Ac 52~56% J. inwald, J. Crandall, W. E. ymans, rg. Synth., Coll. Vol. 5, 863 (1973). 2 g(ac) C 2 3 Et 2 gac NaB 4 2, Et 2 Na J. M. Jerkunica, T. G. Traylor, rg. Synth., Coll. Vol. 6, 766 (1988). C 2 g(ac) 2 C 2 gac. E. Carter,. D. West, rg. Synth., Coll. Vol. 3, 774 (1955). 1) K 2) 2 N 2 81~86% C 2 C 2 1) 2) N 3 1) Na/ 2 2) N 3 N 2 dl-serine C 2 30~40% overall yield

4 ( ) 2 C C B 3, TF ( ) 2 C ( ) 2 C C B (C 2 ) 5 C C 2 disiamylborane Na, 2 2 C B (C 2 ) 7 (C 2 ) 7 ( ) 2 CC ~75%. Kono, J. ooz, rg. Synth., Coll. Vol. 6, 919 (1988). 1) [( ) 2 CC] 2 B TF 1) Li, EtN 2, 2 N 2) 2 2) Na, % 18% E. M. Kaiser, R. A. Benkeser, rg. Synth., Coll. Vol. 6, 852 (1988). B 3, TF B NaB ()-!-pinene G. W. Kabalka, J. T. Maddox, T. Shoup, K. R. Bowers, rg. Synth., Coll. Vol. 9, 522 (1998). C 2 C 2 B 3, TF B C 2 C 2 ( )-!-pinene 2 J. J. Partridge, N. K. Chadha, M. R. Uskokovoc, rg. Synth., Coll. Vol. 7, 339 (1990).

5 C C g, 2 S 4, 2 C 60 C 65~67% G.W. Stacy, R.A. Mikulec, rg. Synth., Coll. Vol. 4, 13 (1963). g, 2 S 4, 2! 76~82% M.S. Newman, W.R. Reichle, rg. Synth., Coll. Vol. 5, 1024 (1973). 2, C 4 0 C 96~98% J. R. Johnson, W. L. McEwen, rg. Synth., Coll. Vol. 1, 521 (1941). 2, Et C 4 5 to 1 C 95%. R. Snyder, L. A. ooks, rg. Synth., Coll. Vol. 2, 171 (1943). 2 C C 2 2, 2 2 C C 2 reflux! 72~84%. S. Rhinesmith, rg. Synth., Coll. Vol. 2, 177 (1943).

6 C C C C 2 2 C 4, 0 C C 2 83~85% T. W. Abbott, D. Althousen, rg. Synth., Coll. Vol. 2, 270 (1943). C C C 2 C 4, dark 52~57% N.. Cromwell, R. Benson, rg. Synth., Coll. Vol. 3, 105 (1955). Ac 2 Et Ac Et Et 62~64% S. M. McElvain, D. Kundiger, rg. Synth., Coll. Vol. 3, 123 (1955). (C 2 ) 4 Ac 2 (C 2 ) 4 C 4 Ac P. Z. Bedoukian, rg. Synth., Coll. Vol. 3, 127 (1955). 2 Et 77~81% K Et 66~69% L.I. Smith, M. M. Falkof, rg. Synth., Coll. Vol. 3, 350 (1955). NBS 2, DMS 80~90% A.W. Langman, D.R. Dalton, rg. Synth., Coll. Vol. 6, 184 (1988).

7 2 C 3 70% 1) K, Et 2), 2 82~88% C 2 R. C. Fuson, J. W. Kneisley, E. W. Kaiser, rg. Synth., Coll. Vol. 3, 209 (1955). (C 2 ) 4 (C 2 ) 7 C 2 *,$-./0123( 2 glycerol (C 2 ) 4!" (C2 ) 7 C 2 1) Zn,, Et 2) Na, Et 3) 2 S 4 (C 2 ) 4 linoleic acid #$%&'() (C 2 ) 7 C 2 J. W. McCutcheon, rg. Synth., Coll. Vol. 3, 526 (1955). C 2 C CC 2 C CC 2 C C(C 2 ) 7 C 2 1) Zn,, Et!"#$%&'()* C 2 C CC 2 C CC 2 C C(C 2 ) 7 C 2 2) Na, Et C 2 C CC 2 C CC 2 C C(C 2 ) 7 C 2 3) 2 S 4 linolenic acid,-./01 2 Et 2 J. W. McCutcheon, rg. Synth., Coll. Vol. 3, 531 (1955). C 8 17 C , Ac NaAc, Et 2 L. F. Fieser, rg. Synth., Coll. Vol. 4, 195 (1963).

8 2 (C 2 ) 7 C C(C 2 ) 7 C 2 (C 2 ) 7 C C(C 2 ) 7 C 2 methyl oleate 1) K, (C 2 ) 7 (C 2 ) 7 C 2 2) 33~42%. Adkins, R. E. Burks, Jr, rg. Synth., Coll. Vol. 3, 785 (1955). (C 2 ) 7 C oleic acid C(C 2 ) 7 C 2 2 Et 2 1) NaN 2 2) (C 2 ) 7 C (C 2 ) 7 C(C 2 ) 7 C 2 (C 2 ) 7 C 2 52~62% N. A. Khan, F. E. Deatherage, J. B. own, rg. Synth., Coll. Vol. 4, 851 (1963). (C 2 ) 8 C 2 2, Et 2 0 C 1) NaN 2 (C 2 ) 8 C 2 (C 2 ) 8 C 2 2) 38~49% N. A. Khan, rg. Synth., Coll. Vol. 4, 969 (1963). 2, C 3 C 2 2, 65 C L. A. Paquette, J.. Barrett, rg. Synth., Coll. Vol. 5, 467 (1973). 2, Et 2 78 C E. Vogel, W. Klug, A. euer, rg. Synth., Coll. Vol. 6, 862 (1988).

9 2, Et 2 30 to 10 C R. Paul,. Riobé, M. Maumy, rg. Synth., Coll. Vol. 6, 675 (1988). C( ) C(C 3 3 ) 3 2 C ( ) 3 C 3 C 2 ( ) 3 C W. Weyler, Jr, W. G. Duncan, M. B. Liewen,. W. Moore, rg. Synth., Coll. Vol. 6, 210 (1988). g 2, Na 2, N 3, 2 70~73% G.. Coleman,.F. Johnstone, rg. Synth., Coll. Vol. 1, 158 (1941). C CC 2, 2 C! C CC 2 C C C G.A. Ropp, W.E. Creig, V. Raaen, rg. Synth., Coll. Vol. 4, 130 (1963). Ac, 2.B. Donahoe, C.A. Vanderwerf, rg. Synth., Coll. Vol. 4, 157 (1963).

10 2 1,2-!" 1,4-!" 60 C 80~75 20~25 25 C C 1,2-!" 1,4-!" CS 2 C 3 C 4 hexane L.F. atch, P.D. Gardner, R.E. Gilbert, J. Am. Chem. Soc., 81, 5943 (1959). 1,2-!" 1,4-!" #$ C M.S. Kharasch, E.T. Margolis, F.A. Mayo, J. rg. Chem., 1, 393 (1936). N 2 25 C 96% Y. Pocker, K.D. Stevens, J.J. Champoux, J. Am. Chem. Soc., 91, 4199 (1969).

11 , 0 C R. B. Moffett, rg. Synth., Coll. Vol. 4, 238 (1963). D D D solvent temp./ C 1,2-!" 1,4-!" Ac N pentane J.E. Nordlander, P.. wuor, J.E. aky, J. Am. Chem. Soc., 101, 1288 (1979).

1 1 H Li Be Na M g B A l C S i N P O S F He N Cl A e K Ca S c T i V C Mn Fe Co Ni Cu Zn Ga Ge As Se B K Rb S Y Z Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb T e

1 1 H Li Be Na M g B A l C S i N P O S F He N Cl A e K Ca S c T i V C Mn Fe Co Ni Cu Zn Ga Ge As Se B K Rb S Y Z Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb T e No. 1 1 1 H Li Be Na M g B A l C S i N P O S F He N Cl A e K Ca S c T i V C Mn Fe Co Ni Cu Zn Ga Ge As Se B K Rb S Y Z Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb T e I X e Cs Ba F Ra Hf Ta W Re Os I Rf Db Sg Bh

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