Chem634_F11_PS05_Key

Chem634_F11_PS05_Key - F F me ~ e h I [IT i Me 5 Sufiglu...

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Unformatted text preview: F F me ~ e h I [IT i Me 5 Sufiglu enaml-jmgr :3 f : J 3? fig" a? P ELM; I“, WI "u; __ gm 3 E. \r/ J“) I flaw” \? L f1 M m a.) I fiWWMJ rid—M .6 ca.- lfibuivi k; (WIT! 11:44 5‘? fiao'rfllibf) rib (“nib ‘f- {Au-":4 «2/ 4km W'H‘ gynfiwifir: P HIE-F [:3 dc: Ag» WW Pk IPD I M .) Maumlfl-IQML} TL?” 0 Cl UFéPa!‘ W? flip r:- '3 LAN- agwfifn my LiU-JECIH m 6H P ,A r MflgLfiJ-de .. ' ILL J Q LDA-fcxcwa}. l‘len ’2, lo) Mewgeph P «3.). U s 5% 9m m 55;; Herr fi—chfls-r E anornfig fi'vHS- Far-{Em 9"“"4'3 I'ubir '9 1:: ML - 9 all x. . MN :1 a film (9 n. i—a a \.J\”% NW H g A“ I H W H . 11" ? C!) it? D BUztirLfi'1.Pr;:‘JEt.1h.=,-n 5"” B :9 -—-r w; “fa-a -' Mr: H :14 F. I'"—' “5"”- T G 1. - 1 f Tnsf: up. " ‘ 5w; :2 Hot fa FGA and C-X OSiR3 FG' OSiR3 FGA OSiR3 :: 2:17;) :> Me Me Me Me Me Me Ph 2 Ph Ph Ph FGI \ o \ O \ asy alkylation \ O ' :—___—:> EAR): ::._—> __———_—;:> {,5‘; R,» i i l L R" o i 1 Me Me Me Me Me (KW Me Ph Me . \ O asy. alkylatlon + :2} Br R* Me Me Me [OX] Me Me PG Me Me 0304 :::> : BnO ; - :: Bf‘lO :- L (3X6 O><O OH OH Me Me Me Me 3 *R O asy. aldol Me FGI Me it Me Me FGI Me fl Bno :.————> BnOVuLLJWTR BnOM _—_——_> BnoJ\/E / *R o (I) O OH OH 1/ asy. alkylation Me _——_—._.—:> BnoW |\ITR* Br 0 I- M Grinard + e M . . FGI _ . 9 Me 3 Me R38IO Mei—l O H MeOAC 4 ring opening ozone H, Me FG| 2:) m /\ l. .~ : R PO JP: 0 Me )xo Me Me epoxidation O=/—>’/ ring closing Me —__—_—_——__> “[3] Eu BOTf Et CHzcak ~78 °C; McCHO; (b)TBSC1, lmidazolc. 13w; {91859321, friaojg; (as) 1233?} 5;? gig); {i} 9 Ni’hécSiMcgh, TH F1 «~73 ~4- «50 °C: Mb: u) Lamb TH F; (k;- tCICOJE? DMSO. Eng: MEOzC . —— 35 2 2. .. .. . . {m1 Hz, (RMNBDmIPHOSIBu CHgClz: (n) Pyr-S‘Os, EI3N. mm. «a T? a /l K0 v" 9 L '2 ® 313 Scheme V!“ (T80 3‘ ata) LDA.THF,~~-:sac; PhC.H~m_=CHCHan-~40°C 0°C: {b} LiAIHJHRo :2. " - 3: « éél,0°C:NaLMazco,ss °C; (d) KHE, LDA. HMPA. THF, «~78 0C; St; (a) HCHaq). 100 °C; NaOH; (f) LiAlH4. 5120; (g) TBD?SC1.EL3N, {)MF; (i1) 03% RICH: :‘QaBH‘p 3C1}: Na], Mcgjco; Pm. McCN. 50 9c: m <1“:th mama CH2CE2; MCPBA,CH2C12. HEOEEIOH: (i) Mesa-2:31, EtJN, CH Sc heme Vm LQASK m 303 800 . 80% 15 31 28 0 Scheme 1X“ . . / BnO I? i o o o o 493* Mexm 39b Maxim: 0 OC: F330; MCOH; (c) p'TOISQg'CI, N, DMAP, CHgClgz (g) M620 am Bulgomagq, CH2613,~78 cc‘ 23, ~78 °C; H202, MeOH; (b) Bugs, HOM, THF; LiBH.” THF. Pyr, 5 °C: ({1} Li[Et}38H. THF; H302. NaOHéaq)‘ MCOH; (6%) 0504. RJNO. H30! MegCO: (f) TBQPSCL E11 (OMeh, CSA‘ M32630: 0:} (22.310345 THF: (i) 9319803, Bram. MSO; <3) K3603. Mc-OH. 44b 44a (a) seesaw. Etgbi. (3:426:23 43 *c: {b} MCPBA, ems. Scheme XI!“ 0(a) PhMgBr, TH F; (b) CpfliCKCHQMMQ, i’yr, THijo acne, ~43 °£ - (1c) McMan CH3C12/EiEO. ~78 °Cz {f} ?BSOT1’. ELJN. CHzC 0 °C: {jg} H2. MeQCO: {1) PPh;. ToiucncheCN‘. 75 °C; ...
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This note was uploaded on 12/21/2011 for the course CHEM 634 taught by Professor Fox,j during the Fall '08 term at University of Delaware.

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Chem634_F11_PS05_Key - F F me ~ e h I [IT i Me 5 Sufiglu...

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